catena-Poly[[methano­lcopper(II)potassium(I)]-μ3-1-(3-meth­oxy-2-oxidobenzyl­ideneamino)-2-(2-oxidobenzamido)ethane]

Luo, W.-X.; Yu, M.-M.; Zheng, L.; Cui, A.-L.; Kou, H.-Z.

doi:10.1107/S1600536807027717

catena-Poly[[methanolcopper(II)potassium(I)]-μ₃-1-(3-methoxy-2-oxidobenzylideneamino)-2-(2-oxidobenzamido)ethane]

W.-X. Luo, M.-M. Yu, L. Zheng, A.-L. Cui and H.-Z. Kou

In the title compound, [CuK(C₁₇H₁₅N₂O₄)(CH₃OH)]_n, the Cu^II ion has a square-planar coordination geometry and is coordinated by two N and two O atoms. One phenoxo and the amide O atom also interact with the methanol-coordinated K⁺ ion along with the methoxy O atom of the trianion. Two bridging interactions to K⁺ give rise to a linear chain structure. The chains are further linked by hydrogen bonds involving the amido methanol O atoms into a two-dimensional network structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027717/ng2273sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027717/ng2273Isup2.hkl Contains datablock I

CCDC reference: 654730

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.042
wR factor = 0.091
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.

Author Response: We used an IP diffractometer to collect the data. Therefore, no standard reflections have been used during the measurement.

DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Author Response: We used an IP diffractometer to collect the data. Therefore, no standard reflections have been used during the measurement.


Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        600 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      37.00 A   3 

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.29

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

1-(2-hydroxybenzamido)-2-(2-hydroxy-3-methoxybenzylideneamino)ethane, abbreviated as H₃L, is an excellent bridging ligand that can link two metal atoms via the phenolato and the amido oxgen atoms to form polynuclear complexes (Kido et al., 2000). A few cyclic heterometallic tetranuclear complexes have been synthesize and their structures have been characterized by diffraction analysis and magnetic studies (Hamamatsu et al., 2007; Kido et al., 2003; Osa et al., 2003). The syntheses requires K[CuL] as the starting reactant. This compound crystallizes from methanol as the title compound.

The structure consists of [CuL]^- and [K(MeOH)]⁺ moieties connected by the phenolato and amido oxygen atoms (Fig. 1). The coordination geometry of potassium is an octahedron, and that of copper is a square plane. Two N atoms and two O atoms are linked to the copper atom. The coordination environment is similar to those found in other cyclic heterometallic tetranuclear complexes.

The phenolato oxygen and amido oxgen atoms are involving in bridging to form a ladder structure (Fig. 2). Adjacent ladders are further linked by hydrogen bonds (involving the amido group and the methanol molecule) (O···O 2.702 (4) Å) to form a two-dimensional, hydrogen-bonded network.

Related literature top

For other polynuclear complexes, see Kido et al. (2003, 2007); Osa et al., 2003. For related literature, see: Hamamatsu et al. (2007); Kido et al. (2000).

Experimental top

The compound was prepared according to the literature method (Kido et al., 2003), and recrystallization from methanol afforded violet, block-shaped crystals.

Structure description top

For other polynuclear complexes, see Kido et al. (2003, 2007); Osa et al., 2003. For related literature, see: Hamamatsu et al. (2007); Kido et al. (2000).

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2004); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XP.

Figures top

	Fig. 1. A view of complex (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Symmetry code: i -x, 1 - y, -z; ii 1 - x, 1 - y, -z.
	Fig. 2. The hydrogen-bonded layer structure.

catena-Poly[[methanolcopper(II)potassium(I)]-µ₃– 1-(3-methoxy-2-oxidobenzylideneamino)-2-(2-oxidobenzamido)ethane] top

Crystal data top

[CuK(C₁₇H₁₅N₂O₄)(CH₄O)]	Z = 2
M_r = 445.99	F(000) = 458
Triclinic, P1	D_x = 1.596 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.851 (6) Å	Cell parameters from 4201 reflections
b = 9.139 (6) Å	θ = 3.0–27.5°
c = 12.458 (6) Å	µ = 1.43 mm⁻¹
α = 72.19 (2)°	T = 293 K
β = 77.68 (3)°	Block, violet
γ = 78.69 (2)°	0.2 × 0.2 × 0.18 mm
V = 928.0 (10) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4201 independent reflections
Radiation source: fine-focus sealed tube	3241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 0.1 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
T_min = 0.732, T_max = 0.759	l = −16→14
9074 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.01P)² + P] where P = (F_o² + 2F_c²)/3
4201 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[CuK(C₁₇H₁₅N₂O₄)(CH₄O)]	γ = 78.69 (2)°
M_r = 445.99	V = 928.0 (10) Å³
Triclinic, P1	Z = 2
a = 8.851 (6) Å	Mo Kα radiation
b = 9.139 (6) Å	µ = 1.43 mm⁻¹
c = 12.458 (6) Å	T = 293 K
α = 72.19 (2)°	0.2 × 0.2 × 0.18 mm
β = 77.68 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4201 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3241 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.759	R_int = 0.045
9074 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.02	Δρ_max = 0.55 e Å⁻³
4201 reflections	Δρ_min = −0.40 e Å⁻³
246 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
Cu1	0.27702 (4)	0.27166 (4)	0.12226 (3)	0.03185 (11)
K1	0.03569 (8)	0.65451 (7)	0.05460 (6)	0.03864 (17)
O1	0.2426 (2)	0.4267 (2)	−0.01471 (17)	0.0358 (5)
O2	0.0917 (2)	0.3708 (2)	0.20129 (17)	0.0358 (5)
N2	0.3005 (3)	0.0990 (3)	0.2574 (2)	0.0325 (5)
N1	0.4802 (3)	0.1843 (3)	0.0599 (2)	0.0344 (6)
C16	0.3546 (3)	0.4689 (3)	−0.1033 (2)	0.0311 (6)
C11	0.5110 (3)	0.3922 (3)	−0.1150 (3)	0.0324 (6)
O3	0.7203 (2)	0.2010 (3)	−0.0501 (2)	0.0442 (5)
C1	0.0455 (3)	0.3377 (3)	0.3110 (3)	0.0314 (6)
C2	−0.0732 (4)	0.4438 (3)	0.3569 (3)	0.0350 (7)
C7	0.2269 (4)	0.0894 (3)	0.3583 (3)	0.0359 (7)
H7A	0.2556	0.0012	0.4153	0.043*
C12	0.6138 (4)	0.4529 (4)	−0.2151 (3)	0.0414 (7)
H12A	0.7163	0.4038	−0.2241	0.050*
C8	0.4203 (4)	−0.0246 (3)	0.2303 (3)	0.0413 (7)
H8A	0.3758	−0.0905	0.2010	0.050*
H8B	0.4613	−0.0879	0.2987	0.050*
C10	0.5754 (3)	0.2510 (3)	−0.0307 (3)	0.0328 (6)
C6	0.1032 (3)	0.2026 (3)	0.3925 (3)	0.0336 (6)
C4	−0.0790 (5)	0.2770 (4)	0.5471 (3)	0.0513 (9)
H4A	−0.1221	0.2557	0.6243	0.062*
C15	0.3135 (4)	0.6004 (4)	−0.1913 (3)	0.0394 (7)
H15A	0.2120	0.6524	−0.1840	0.047*
C13	0.5699 (4)	0.5814 (4)	−0.3001 (3)	0.0477 (8)
H13A	0.6415	0.6179	−0.3650	0.057*
C9	0.5501 (4)	0.0481 (4)	0.1414 (3)	0.0411 (7)
H9A	0.6202	0.0791	0.1780	0.049*
H9B	0.6098	−0.0264	0.1017	0.049*
C5	0.0393 (4)	0.1755 (4)	0.5088 (3)	0.0438 (8)
H5A	0.0784	0.0865	0.5608	0.053*
C3	−0.1347 (4)	0.4125 (4)	0.4699 (3)	0.0489 (8)
H3A	−0.2148	0.4823	0.4958	0.059*
C14	0.4183 (4)	0.6552 (4)	−0.2879 (3)	0.0445 (8)
H14A	0.3868	0.7421	−0.3449	0.053*
C17	−0.2533 (4)	0.6761 (4)	0.3077 (3)	0.0544 (9)
H17A	−0.3396	0.6178	0.3350	0.082*
H17B	−0.2751	0.7612	0.2427	0.082*
H17C	−0.2377	0.7154	0.3672	0.082*
O4	−0.1159 (3)	0.5782 (2)	0.27564 (19)	0.0434 (5)
O5	−0.1113 (3)	0.9268 (3)	−0.06939 (19)	0.0465 (6)
C18	0.0008 (4)	0.9855 (4)	−0.1635 (3)	0.0485 (8)
H18C	−0.0447	1.0816	−0.2103	0.073*
H18D	0.0358	0.9119	−0.2076	0.073*
H18A	0.0880	1.0031	−0.1369	0.073*
H5	−0.1666	0.9996	−0.0431	0.051 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02267 (18)	0.0323 (2)	0.0352 (2)	0.00534 (14)	−0.00369 (14)	−0.00796 (15)
K1	0.0325 (4)	0.0315 (3)	0.0475 (4)	0.0003 (3)	−0.0073 (3)	−0.0071 (3)
O1	0.0230 (10)	0.0383 (11)	0.0373 (11)	0.0031 (9)	−0.0011 (8)	−0.0051 (9)
O2	0.0295 (11)	0.0350 (11)	0.0335 (11)	0.0051 (9)	0.0009 (9)	−0.0060 (9)
N2	0.0260 (13)	0.0281 (12)	0.0404 (14)	0.0042 (10)	−0.0064 (11)	−0.0094 (10)
N1	0.0241 (12)	0.0313 (13)	0.0436 (15)	0.0057 (10)	−0.0048 (11)	−0.0109 (11)
C16	0.0279 (15)	0.0329 (15)	0.0333 (15)	−0.0044 (12)	0.0013 (12)	−0.0145 (12)
C11	0.0268 (15)	0.0351 (15)	0.0390 (16)	−0.0021 (12)	−0.0017 (12)	−0.0196 (13)
O3	0.0213 (11)	0.0412 (13)	0.0683 (15)	0.0018 (9)	0.0018 (10)	−0.0223 (11)
C1	0.0239 (14)	0.0300 (14)	0.0384 (16)	−0.0044 (11)	−0.0005 (12)	−0.0094 (12)
C2	0.0331 (16)	0.0312 (15)	0.0394 (17)	−0.0031 (13)	−0.0032 (13)	−0.0105 (13)
C7	0.0370 (17)	0.0283 (15)	0.0382 (17)	−0.0015 (13)	−0.0096 (13)	−0.0029 (12)
C12	0.0313 (17)	0.0494 (19)	0.0463 (19)	−0.0108 (14)	0.0043 (14)	−0.0213 (15)
C8	0.0355 (17)	0.0314 (16)	0.053 (2)	0.0070 (13)	−0.0089 (15)	−0.0121 (14)
C10	0.0244 (14)	0.0320 (15)	0.0464 (18)	0.0024 (12)	−0.0046 (13)	−0.0218 (13)
C6	0.0314 (16)	0.0311 (15)	0.0365 (16)	−0.0056 (12)	−0.0026 (12)	−0.0082 (12)
C4	0.060 (2)	0.053 (2)	0.0355 (18)	−0.0069 (18)	0.0074 (16)	−0.0154 (16)
C15	0.0357 (17)	0.0386 (17)	0.0408 (17)	0.0005 (14)	−0.0030 (14)	−0.0121 (14)
C13	0.048 (2)	0.053 (2)	0.0407 (19)	−0.0169 (17)	0.0088 (15)	−0.0162 (16)
C9	0.0300 (16)	0.0368 (17)	0.052 (2)	0.0101 (13)	−0.0085 (14)	−0.0142 (15)
C5	0.050 (2)	0.0398 (18)	0.0374 (17)	−0.0071 (15)	−0.0047 (15)	−0.0060 (14)
C3	0.050 (2)	0.047 (2)	0.047 (2)	−0.0006 (16)	0.0064 (16)	−0.0215 (16)
C14	0.054 (2)	0.0429 (18)	0.0345 (17)	−0.0118 (16)	−0.0017 (15)	−0.0080 (14)
C17	0.041 (2)	0.047 (2)	0.069 (2)	0.0122 (16)	−0.0041 (18)	−0.0220 (18)
O4	0.0370 (13)	0.0357 (12)	0.0485 (13)	0.0106 (10)	−0.0024 (10)	−0.0113 (10)
O5	0.0439 (14)	0.0376 (13)	0.0495 (14)	0.0036 (11)	−0.0018 (11)	−0.0096 (11)
C18	0.0379 (19)	0.048 (2)	0.053 (2)	−0.0013 (16)	−0.0014 (16)	−0.0107 (16)

Geometric parameters (Å, º) top

Cu1—O1	1.893 (2)	C7—H7A	0.9300
Cu1—N1	1.922 (3)	C12—C13	1.374 (5)
Cu1—O2	1.937 (2)	C12—H12A	0.9300
Cu1—N2	1.940 (3)	C8—C9	1.515 (5)
K1—O2	2.701 (3)	C8—H8A	0.9700
K1—O1	2.714 (2)	C8—H8B	0.9700
K1—O3ⁱ	2.726 (3)	C6—C5	1.402 (4)
K1—O4	2.736 (3)	C4—C5	1.364 (5)
K1—O5	2.740 (3)	C4—C3	1.392 (5)
K1—O1ⁱⁱ	2.886 (3)	C4—H4A	0.9300
O1—C16	1.331 (3)	C15—C14	1.377 (5)
O1—K1ⁱⁱ	2.886 (3)	C15—H15A	0.9300
O2—C1	1.298 (4)	C13—C14	1.378 (5)
N2—C7	1.272 (4)	C13—H13A	0.9300
N2—C8	1.457 (4)	C9—H9A	0.9700
N1—C10	1.315 (4)	C9—H9B	0.9700
N1—C9	1.469 (4)	C5—H5A	0.9300
C16—C15	1.403 (4)	C3—H3A	0.9300
C16—C11	1.423 (4)	C14—H14A	0.9300
C11—C12	1.407 (4)	C17—O4	1.422 (4)
C11—C10	1.494 (4)	C17—H17A	0.9600
O3—C10	1.272 (3)	C17—H17B	0.9600
O3—K1ⁱ	2.726 (3)	C17—H17C	0.9600
C1—C6	1.422 (4)	O5—C18	1.406 (4)
C1—C2	1.433 (4)	O5—H5	0.8521
C2—C3	1.358 (5)	C18—H18C	0.9600
C2—O4	1.377 (4)	C18—H18D	0.9600
C7—C6	1.441 (4)	C18—H18A	0.9600

O1—Cu1—N1	95.19 (10)	N2—C8—C9	108.7 (3)
O1—Cu1—O2	88.75 (9)	N2—C8—H8A	110.0
N1—Cu1—O2	169.99 (10)	C9—C8—H8A	110.0
O1—Cu1—N2	173.78 (10)	N2—C8—H8B	110.0
N1—Cu1—N2	85.22 (11)	C9—C8—H8B	110.0
O2—Cu1—N2	91.86 (10)	H8A—C8—H8B	108.3
O2—K1—O1	59.32 (7)	O3—C10—N1	123.1 (3)
O2—K1—O3ⁱ	104.21 (8)	O3—C10—C11	118.2 (3)
O1—K1—O3ⁱ	89.14 (8)	N1—C10—C11	118.7 (2)
O2—K1—O4	57.36 (7)	C5—C6—C1	120.4 (3)
O1—K1—O4	116.65 (7)	C5—C6—C7	118.2 (3)
O3ⁱ—K1—O4	107.21 (8)	C1—C6—C7	121.4 (3)
O2—K1—O5	162.88 (7)	C5—C4—C3	119.4 (3)
O1—K1—O5	130.64 (8)	C5—C4—H4A	120.3
O3ⁱ—K1—O5	90.63 (9)	C3—C4—H4A	120.3
O4—K1—O5	110.44 (8)	C14—C15—C16	122.3 (3)
O2—K1—O1ⁱⁱ	90.43 (7)	C14—C15—H15A	118.8
O1—K1—O1ⁱⁱ	97.52 (7)	C16—C15—H15A	118.8
O3ⁱ—K1—O1ⁱⁱ	165.31 (7)	C12—C13—C14	119.0 (3)
O4—K1—O1ⁱⁱ	81.53 (8)	C12—C13—H13A	120.5
O5—K1—O1ⁱⁱ	75.08 (8)	C14—C13—H13A	120.5
C16—O1—Cu1	124.07 (18)	N1—C9—C8	108.6 (2)
C16—O1—K1	117.80 (17)	N1—C9—H9A	110.0
Cu1—O1—K1	104.65 (9)	C8—C9—H9A	110.0
C16—O1—K1ⁱⁱ	118.66 (17)	N1—C9—H9B	110.0
Cu1—O1—K1ⁱⁱ	100.64 (9)	C8—C9—H9B	110.0
K1—O1—K1ⁱⁱ	82.48 (7)	H9A—C9—H9B	108.4
C1—O2—Cu1	126.37 (18)	C4—C5—C6	121.4 (3)
C1—O2—K1	124.59 (17)	C4—C5—H5A	119.3
Cu1—O2—K1	103.83 (9)	C6—C5—H5A	119.3
C7—N2—C8	122.0 (3)	C2—C3—C4	120.7 (3)
C7—N2—Cu1	127.1 (2)	C2—C3—H3A	119.7
C8—N2—Cu1	110.9 (2)	C4—C3—H3A	119.7
C10—N1—C9	116.5 (2)	C15—C14—C13	120.0 (3)
C10—N1—Cu1	127.7 (2)	C15—C14—H14A	120.0
C9—N1—Cu1	113.3 (2)	C13—C14—H14A	120.0
O1—C16—C15	116.7 (3)	O4—C17—H17A	109.5
O1—C16—C11	125.2 (3)	O4—C17—H17B	109.5
C15—C16—C11	118.1 (3)	H17A—C17—H17B	109.5
C12—C11—C16	117.5 (3)	O4—C17—H17C	109.5
C12—C11—C10	117.0 (3)	H17A—C17—H17C	109.5
C16—C11—C10	125.6 (3)	H17B—C17—H17C	109.5
C10—O3—K1ⁱ	127.29 (18)	C2—O4—C17	117.3 (3)
O2—C1—C6	125.4 (3)	C2—O4—K1	123.72 (17)
O2—C1—C2	118.9 (3)	C17—O4—K1	118.8 (2)
C6—C1—C2	115.7 (3)	C18—O5—K1	105.91 (19)
C3—C2—O4	124.5 (3)	C18—O5—H5	110.9
C3—C2—C1	122.2 (3)	K1—O5—H5	126.3
O4—C2—C1	113.2 (3)	O5—C18—H18C	109.5
N2—C7—C6	126.0 (3)	O5—C18—H18D	109.5
N2—C7—H7A	117.0	H18C—C18—H18D	109.5
C6—C7—H7A	117.0	O5—C18—H18A	109.5
C13—C12—C11	123.1 (3)	H18C—C18—H18A	109.5
C13—C12—H12A	118.4	H18D—C18—H18A	109.5
C11—C12—H12A	118.4

N1—Cu1—O1—C16	−15.7 (2)	K1—O2—C1—C6	−164.0 (2)
O2—Cu1—O1—C16	155.1 (2)	Cu1—O2—C1—C2	166.0 (2)
K1ⁱⁱ—Cu1—O1—C16	−135.7 (2)	K1—O2—C1—C2	15.8 (4)
N1—Cu1—O1—K1	−155.04 (10)	O2—C1—C2—C3	175.7 (3)
O2—Cu1—O1—K1	15.73 (9)	C6—C1—C2—C3	−4.5 (4)
N1—Cu1—O1—K1ⁱⁱ	120.04 (10)	O2—C1—C2—O4	−4.8 (4)
O2—Cu1—O1—K1ⁱⁱ	−69.19 (9)	C6—C1—C2—O4	175.1 (3)
O2—K1—O1—C16	−155.5 (2)	C8—N2—C7—C6	−177.6 (3)
O3ⁱ—K1—O1—C16	−48.4 (2)	Cu1—N2—C7—C6	3.8 (5)
O4—K1—O1—C16	−157.23 (18)	C16—C11—C12—C13	0.2 (5)
O5—K1—O1—C16	41.7 (2)	C10—C11—C12—C13	179.5 (3)
O1ⁱⁱ—K1—O1—C16	118.5 (2)	C7—N2—C8—C9	−142.6 (3)
O3ⁱ—K1—O1—Cu1	94.05 (10)	Cu1—N2—C8—C9	36.3 (3)
O4—K1—O1—Cu1	−14.83 (12)	K1ⁱ—O3—C10—N1	−114.3 (3)
O5—K1—O1—Cu1	−175.86 (8)	K1ⁱ—O3—C10—C11	65.8 (3)
O1ⁱⁱ—K1—O1—Cu1	−99.09 (10)	C9—N1—C10—O3	1.4 (4)
O2—K1—O1—K1ⁱⁱ	86.02 (8)	Cu1—N1—C10—O3	162.2 (2)
O3ⁱ—K1—O1—K1ⁱⁱ	−166.86 (7)	C9—N1—C10—C11	−178.6 (2)
O4—K1—O1—K1ⁱⁱ	84.26 (8)	Cu1—N1—C10—C11	−17.8 (4)
O5—K1—O1—K1ⁱⁱ	−76.77 (10)	C12—C11—C10—O3	4.8 (4)
O1ⁱⁱ—K1—O1—K1ⁱⁱ	0.0	C16—C11—C10—O3	−176.0 (3)
Cu1ⁱⁱ—K1—O1—K1ⁱⁱ	−29.86 (5)	C12—C11—C10—N1	−175.2 (3)
O1—Cu1—O2—C1	−170.9 (2)	C16—C11—C10—N1	4.1 (4)
N1—Cu1—O2—C1	−57.5 (7)	O2—C1—C6—C5	−177.1 (3)
N2—Cu1—O2—C1	15.3 (2)	C2—C1—C6—C5	3.1 (4)
K1ⁱⁱ—Cu1—O2—C1	141.3 (2)	O2—C1—C6—C7	2.2 (5)
O1—Cu1—O2—K1	−15.75 (9)	C2—C1—C6—C7	−177.6 (3)
N1—Cu1—O2—K1	97.6 (6)	N2—C7—C6—C5	−177.6 (3)
N2—Cu1—O2—K1	170.44 (9)	N2—C7—C6—C1	3.1 (5)
O1—K1—O2—C1	168.4 (2)	O1—C16—C15—C14	−179.5 (3)
O3ⁱ—K1—O2—C1	88.1 (2)	C11—C16—C15—C14	0.9 (5)
O4—K1—O2—C1	−13.4 (2)	C11—C12—C13—C14	0.0 (5)
O5—K1—O2—C1	−61.3 (3)	C10—N1—C9—C8	−172.4 (3)
O1ⁱⁱ—K1—O2—C1	−93.1 (2)	Cu1—N1—C9—C8	24.0 (3)
K1ⁱⁱ—K1—O2—C1	−135.3 (2)	N2—C8—C9—N1	−38.5 (3)
Cu1ⁱⁱ—K1—O2—C1	−102.8 (2)	C3—C4—C5—C6	−1.8 (6)
O1—K1—O2—Cu1	12.72 (7)	C1—C6—C5—C4	−0.1 (5)
O3ⁱ—K1—O2—Cu1	−67.59 (10)	C7—C6—C5—C4	−179.4 (3)
O4—K1—O2—Cu1	−169.14 (12)	O4—C2—C3—C4	−176.7 (3)
O5—K1—O2—Cu1	143.0 (2)	C1—C2—C3—C4	2.8 (5)
O1ⁱⁱ—K1—O2—Cu1	111.21 (10)	C5—C4—C3—C2	0.5 (6)
N1—Cu1—N2—C7	159.9 (3)	C16—C15—C14—C13	−0.7 (5)
O2—Cu1—N2—C7	−10.5 (3)	C12—C13—C14—C15	0.3 (5)
O2—Cu1—N2—C8	170.7 (2)	C3—C2—O4—C17	−12.8 (5)
K1ⁱⁱ—Cu1—N2—C8	99.6 (2)	C1—C2—O4—C17	167.7 (3)
O1—Cu1—N1—C10	21.4 (3)	C3—C2—O4—K1	171.7 (3)
O2—Cu1—N1—C10	−91.5 (6)	C1—C2—O4—K1	−7.8 (3)
N2—Cu1—N1—C10	−164.9 (3)	O2—K1—O4—C2	10.4 (2)
O1—Cu1—N1—C9	−177.3 (2)	O1—K1—O4—C2	12.2 (2)
O2—Cu1—N1—C9	69.8 (6)	O3ⁱ—K1—O4—C2	−85.7 (2)
N2—Cu1—N1—C9	−3.5 (2)	O5—K1—O4—C2	177.0 (2)
Cu1—O1—C16—C15	−171.1 (2)	O1ⁱⁱ—K1—O4—C2	106.4 (2)
K1—O1—C16—C15	−36.5 (3)	O2—K1—O4—C17	−165.0 (3)
K1ⁱⁱ—O1—C16—C15	60.3 (3)	O1—K1—O4—C17	−163.2 (2)
Cu1—O1—C16—C11	8.5 (4)	O3ⁱ—K1—O4—C17	98.9 (2)
K1—O1—C16—C11	143.1 (2)	O5—K1—O4—C17	1.6 (2)
K1ⁱⁱ—O1—C16—C11	−120.0 (3)	O1ⁱⁱ—K1—O4—C17	−69.0 (2)
O1—C16—C11—C12	179.8 (3)	O2—K1—O5—C18	−159.7 (2)
C15—C16—C11—C12	−0.6 (4)	O1—K1—O5—C18	−39.6 (2)
O1—C16—C11—C10	0.6 (4)	O3ⁱ—K1—O5—C18	49.8 (2)
C15—C16—C11—C10	−179.8 (3)	O4—K1—O5—C18	158.47 (19)
Cu1—O2—C1—C6	−13.8 (4)	O1ⁱⁱ—K1—O5—C18	−126.7 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O3ⁱⁱⁱ	0.85	1.90	2.703 (4)	156

Symmetry code: (iii) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	[CuK(C₁₇H₁₅N₂O₄)(CH₄O)]
M_r	445.99
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.851 (6), 9.139 (6), 12.458 (6)
α, β, γ (°)	72.19 (2), 77.68 (3), 78.69 (2)
V (Å³)	928.0 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.2 × 0.2 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.732, 0.759
No. of measured, independent and observed [I > 2σ(I)] reflections	9074, 4201, 3241
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.091, 1.02
No. of reflections	4201
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.40

Computer programs: CrystalStructure (Rigaku/MSC, 2004), CrystalStructure, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1998), XP.

Selected geometric parameters (Å, º) top

Cu1—O1	1.893 (2)	K1—O1	2.714 (2)
Cu1—N1	1.922 (3)	K1—O3ⁱ	2.726 (3)
Cu1—O2	1.937 (2)	K1—O4	2.736 (3)
Cu1—N2	1.940 (3)	K1—O5	2.740 (3)
K1—O2	2.701 (3)	K1—O1ⁱⁱ	2.886 (3)

O1—Cu1—N1	95.19 (10)	O2—K1—O5	162.88 (7)
O1—Cu1—O2	88.75 (9)	O1—K1—O5	130.64 (8)
N1—Cu1—O2	169.99 (10)	O3ⁱ—K1—O5	90.63 (9)
O1—Cu1—N2	173.78 (10)	O4—K1—O5	110.44 (8)
N1—Cu1—N2	85.22 (11)	O2—K1—O1ⁱⁱ	90.43 (7)
O2—Cu1—N2	91.86 (10)	O1—K1—O1ⁱⁱ	97.52 (7)
O2—K1—O1	59.32 (7)	O3ⁱ—K1—O1ⁱⁱ	165.31 (7)
O2—K1—O3ⁱ	104.21 (8)	O4—K1—O1ⁱⁱ	81.53 (8)
O1—K1—O3ⁱ	89.14 (8)	O5—K1—O1ⁱⁱ	75.08 (8)
O2—K1—O4	57.36 (7)	Cu1—O1—K1ⁱⁱ	100.64 (9)
O1—K1—O4	116.65 (7)	K1—O1—K1ⁱⁱ	82.48 (7)
O3ⁱ—K1—O4	107.21 (8)	Cu1—O2—K1	103.83 (9)