Aqua­(2,2′-bipyridine-κ2N,N′)(l-malato-κ3O,O′,O′′)copper(II)

He, L.

doi:10.1107/S1600536805025274

Aqua(2,2′-bipyridine-κ²N,N′)(L-malato-κ³O,O′,O′′)copper(II)

In the title complex, [Cu(C₄H₄O₅)(C₁₀H₈N₂)(H₂O)], the chiral L-malate group, which acts as a tridentate ligand, the bidentate 2,2′-bipyridine ligand and the water molecule provide an octahedral coordination of the Cu^II atom with strong Jahn–Teller distortion. Intermolecular O—H

O hydrogen bonds stabilize the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025274/cv6564sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025274/cv6564Isup2.hkl Contains datablock I

CCDC reference: 283790

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.028
wR factor = 0.070
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   O3      ..       5.76 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   O5      ..       8.52 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu     -   N2      ..       5.28 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.48
           From the CIF: _reflns_number_total               3102
           Count of symmetry unique reflns         1786
           Completeness (_total/calc)            173.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1316
           Fraction of Friedel pairs measured     0.737
           Are heavy atom types Z>Si present        yes

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Aqua(2,2'-bipyridine-κ²N,N')(L-malato-κ³O,O',O'')copper(II) top

Crystal data top

[Cu(C₄H₄O₅)(C₁₀H₈N₂)(H₂O)]	F(000) = 378
M_r = 369.81	D_x = 1.714 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 5265 reflections
a = 10.4874 (6) Å	θ = 3.7–27.5°
b = 6.5998 (3) Å	µ = 1.56 mm⁻¹
c = 10.7986 (4) Å	T = 293 K
β = 106.570 (2)°	Prism, blue
V = 716.38 (6) Å³	0.30 × 0.23 × 0.09 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	3102 independent reflections
Radiation source: fine-focus sealed tube	2966 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.043
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.657, T_max = 0.869	k = −8→8
6910 measured reflections	l = −14→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.028	w = 1/[σ²(F_o²) + (0.032P)² + 0.1622P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.070	(Δ/σ)_max = 0.001
S = 1.11	Δρ_max = 0.24 e Å⁻³
3102 reflections	Δρ_min = −0.33 e Å⁻³
225 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.0326 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1318 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.028 (11)

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
Cu	0.19669 (2)	0.25000 (5)	0.18940 (2)	0.02741 (10)
O1	0.01430 (14)	0.2499 (5)	0.08411 (14)	0.0332 (3)
O2	−0.18387 (18)	0.3331 (3)	0.10466 (19)	0.0391 (4)
O3	0.11771 (17)	0.1672 (3)	0.33077 (17)	0.0264 (3)
O4	0.04892 (19)	0.8028 (3)	0.35711 (18)	0.0321 (4)
O5	0.15784 (19)	0.5808 (3)	0.27066 (19)	0.0356 (4)
O6	0.2615 (2)	−0.1032 (3)	0.16271 (19)	0.0385 (4)
N1	0.38459 (18)	0.2805 (3)	0.29485 (19)	0.0265 (4)
N2	0.27600 (19)	0.3108 (3)	0.04689 (19)	0.0270 (4)
C1	0.4294 (2)	0.2690 (5)	0.4234 (2)	0.0347 (5)
H1	0.3684	0.2525	0.4704	0.042*
C2	0.5633 (3)	0.2808 (5)	0.4891 (3)	0.0410 (7)
H2	0.5924	0.2707	0.5787	0.049*
C3	0.6526 (3)	0.3079 (5)	0.4181 (3)	0.0439 (7)
H3	0.7432	0.3163	0.4599	0.053*
C4	0.6078 (3)	0.3224 (5)	0.2856 (3)	0.0382 (6)
H4	0.6673	0.3416	0.2372	0.046*
C5	0.4715 (2)	0.3076 (3)	0.2253 (2)	0.0270 (5)
C6	0.4102 (2)	0.3187 (4)	0.0837 (2)	0.0259 (5)
C7	0.4816 (3)	0.3319 (4)	−0.0060 (3)	0.0337 (5)
H7	0.5741	0.3354	0.0205	0.040*
C8	0.4124 (3)	0.3397 (4)	−0.1359 (3)	0.0372 (6)
H8	0.4580	0.3479	−0.1980	0.045*
C9	0.2752 (3)	0.3352 (5)	−0.1724 (2)	0.0361 (6)
H9	0.2274	0.3424	−0.2593	0.043*
C10	0.2095 (3)	0.3199 (4)	−0.0785 (2)	0.0323 (5)
H10	0.1170	0.3158	−0.1032	0.039*
C11	−0.0663 (2)	0.2827 (4)	0.1498 (2)	0.0265 (5)
C12	−0.01219 (19)	0.2583 (5)	0.29726 (19)	0.0238 (4)
C13	−0.0080 (2)	0.4594 (4)	0.3662 (2)	0.0273 (5)
H13A	0.0279	0.4363	0.4583	0.033*
H13B	−0.0985	0.5077	0.3510	0.033*
C14	0.0736 (2)	0.6267 (4)	0.3269 (2)	0.0228 (5)
H31	0.122 (4)	0.050 (6)	0.336 (3)	0.055 (11)*
H12	−0.0722	0.1667	0.3261	0.029*
H61	0.229 (4)	−0.200 (4)	0.196 (3)	0.073 (14)*
H62	0.240 (3)	−0.116 (5)	0.081 (2)	0.052 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.01775 (12)	0.03661 (16)	0.02827 (13)	−0.00101 (14)	0.00719 (8)	0.00198 (16)
O1	0.0221 (7)	0.0489 (9)	0.0284 (7)	−0.0003 (11)	0.0070 (5)	−0.0035 (12)
O2	0.0223 (8)	0.0532 (11)	0.0417 (10)	0.0053 (8)	0.0089 (7)	0.0033 (9)
O3	0.0253 (8)	0.0202 (8)	0.0347 (9)	0.0008 (6)	0.0099 (7)	0.0024 (7)
O4	0.0409 (10)	0.0189 (9)	0.0395 (9)	−0.0030 (6)	0.0163 (7)	−0.0051 (7)
O5	0.0401 (10)	0.0247 (9)	0.0510 (11)	−0.0013 (7)	0.0276 (9)	0.0019 (8)
O6	0.0475 (12)	0.0337 (10)	0.0371 (10)	−0.0116 (9)	0.0166 (9)	−0.0031 (9)
N1	0.0228 (8)	0.0236 (12)	0.0324 (9)	−0.0005 (8)	0.0069 (7)	0.0003 (9)
N2	0.0216 (9)	0.0263 (10)	0.0331 (9)	−0.0006 (7)	0.0079 (7)	0.0019 (8)
C1	0.0332 (11)	0.0356 (15)	0.0344 (11)	−0.0019 (13)	0.0082 (9)	0.0015 (14)
C2	0.0367 (13)	0.043 (2)	0.0350 (11)	−0.0015 (12)	−0.0023 (9)	0.0024 (13)
C3	0.0246 (12)	0.0504 (18)	0.0494 (15)	−0.0025 (11)	−0.0009 (10)	0.0011 (13)
C4	0.0233 (11)	0.0437 (15)	0.0467 (14)	−0.0031 (10)	0.0087 (10)	0.0000 (13)
C5	0.0218 (10)	0.0240 (12)	0.0349 (11)	−0.0011 (8)	0.0076 (8)	−0.0006 (9)
C6	0.0231 (10)	0.0204 (10)	0.0344 (11)	−0.0007 (8)	0.0086 (9)	0.0010 (9)
C7	0.0278 (12)	0.0329 (12)	0.0446 (14)	−0.0013 (10)	0.0171 (10)	0.0012 (11)
C8	0.0446 (15)	0.0309 (13)	0.0436 (14)	−0.0009 (12)	0.0248 (12)	0.0018 (12)
C9	0.0421 (14)	0.0354 (13)	0.0300 (12)	−0.0001 (11)	0.0089 (11)	0.0023 (11)
C10	0.0272 (11)	0.0337 (12)	0.0343 (11)	0.0012 (9)	0.0059 (9)	0.0029 (10)
C11	0.0214 (9)	0.0230 (14)	0.0352 (10)	−0.0024 (8)	0.0080 (8)	−0.0022 (10)
C12	0.0226 (8)	0.0191 (9)	0.0330 (10)	−0.0020 (11)	0.0131 (7)	0.0040 (13)
C13	0.0327 (12)	0.0220 (11)	0.0325 (11)	0.0006 (9)	0.0177 (10)	0.0020 (10)
C14	0.0239 (11)	0.0198 (11)	0.0230 (10)	−0.0017 (8)	0.0038 (8)	0.0012 (9)

Geometric parameters (Å, º) top

Cu—O1	1.9264 (14)	C2—H2	0.9300
Cu—O3	2.0090 (18)	C3—C4	1.376 (4)
Cu—O5	2.4301 (18)	C3—H3	0.9300
Cu—O6	2.468 (2)	C4—C5	1.396 (3)
Cu—N1	1.9850 (19)	C4—H4	0.9300
Cu—N2	1.988 (2)	C5—C6	1.481 (3)
O1—C11	1.267 (3)	C6—C7	1.387 (3)
O2—C11	1.235 (3)	C7—C8	1.384 (4)
O3—C12	1.438 (3)	C7—H7	0.9300
O3—H31	0.77 (4)	C8—C9	1.380 (4)
O4—C14	1.254 (3)	C8—H8	0.9300
O5—C14	1.244 (3)	C9—C10	1.383 (4)
O6—H61	0.85 (3)	C9—H9	0.9300
O6—H62	0.85 (2)	C10—H10	0.9300
N1—C1	1.335 (3)	C11—C12	1.539 (3)
N1—C5	1.348 (3)	C12—C13	1.516 (4)
N2—C10	1.336 (3)	C12—H12	0.9900
N2—C6	1.349 (3)	C13—C14	1.529 (3)
C1—C2	1.383 (3)	C13—H13A	0.9700
C1—H1	0.9300	C13—H13B	0.9700
C2—C3	1.380 (4)

O1—Cu—O3	83.87 (7)	C5—C4—H4	120.6
O1—Cu—O5	88.45 (9)	N1—C5—C4	121.0 (2)
O1—Cu—O6	100.98 (9)	N1—C5—C6	114.7 (2)
O1—Cu—N1	174.12 (13)	C4—C5—C6	124.3 (2)
O1—Cu—N2	96.17 (7)	N2—C6—C7	121.5 (2)
O3—Cu—O5	79.74 (7)	N2—C6—C5	114.3 (2)
O3—Cu—O6	91.05 (7)	C7—C6—C5	124.2 (2)
O3—Cu—N1	98.55 (8)	C8—C7—C6	118.6 (2)
O3—Cu—N2	175.88 (9)	C8—C7—H7	120.7
O5—Cu—O6	166.12 (7)	C6—C7—H7	120.7
O5—Cu—N1	86.73 (8)	C9—C8—C7	119.5 (2)
O5—Cu—N2	104.38 (7)	C9—C8—H8	120.3
O6—Cu—N1	84.38 (8)	C7—C8—H8	120.3
O6—Cu—N2	84.88 (7)	C8—C9—C10	119.3 (2)
N1—Cu—N2	81.81 (8)	C8—C9—H9	120.4
C11—O1—Cu	112.22 (13)	C10—C9—H9	120.4
C12—O3—Cu	105.16 (13)	N2—C10—C9	121.4 (2)
C12—O3—H31	117 (3)	N2—C10—H10	119.3
Cu—O3—H31	108 (3)	C9—C10—H10	119.3
C14—O5—Cu	127.64 (15)	O2—C11—O1	125.1 (2)
H61—O6—H62	110 (3)	O2—C11—C12	117.9 (2)
C1—N1—C5	119.6 (2)	O1—C11—C12	116.97 (18)
C1—N1—Cu	126.04 (16)	O3—C12—C13	110.45 (19)
C5—N1—Cu	114.33 (16)	O3—C12—C11	110.31 (17)
C10—N2—C6	119.7 (2)	C13—C12—C11	111.6 (2)
C10—N2—Cu	125.52 (17)	O3—C12—H12	108.00
C6—N2—Cu	114.26 (16)	C13—C12—H12	108.00
N1—C1—C2	122.4 (2)	C11—C12—H12	108.00
N1—C1—H1	118.8	C12—C13—C14	115.87 (19)
C2—C1—H1	118.8	C12—C13—H13A	108.3
C3—C2—C1	118.2 (2)	C14—C13—H13A	108.3
C3—C2—H2	120.9	C12—C13—H13B	108.3
C1—C2—H2	120.9	C14—C13—H13B	108.3
C4—C3—C2	120.2 (2)	H13A—C13—H13B	107.4
C4—C3—H3	119.9	O5—C14—O4	125.5 (2)
C2—C3—H3	119.9	O5—C14—C13	119.4 (2)
C3—C4—C5	118.7 (3)	O4—C14—C13	115.11 (19)
C3—C4—H4	120.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···O4ⁱ	0.78 (4)	1.84 (4)	2.551 (3)	151 (4)
O6—H61···O5ⁱ	0.85 (3)	1.90 (3)	2.759 (3)	179 (4)
O6—H62···O2ⁱⁱ	0.85 (2)	1.95 (2)	2.799 (3)	175 (3)

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

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Aqua­(2,2′-bipyridine-κ2N,N′)(L-malato-κ3O,O′,O′′)copper(II)

Supporting information

Key indicators

checkCIF/PLATON results

Aqua(2,2′-bipyridine-κ²N,N′)(L-malato-κ³O,O′,O′′)copper(II)