A copper complex of an unusual hy­droxy–carboxyl­ate ligand: [Cu(bpy)(C₄H₄O₆)]

A five-coordinate copper(II) complex with bpy and 2-(hy­droxy­meth­yl)tartronate ligands forms centrosymmetric dimers via Cu...O contacts [2.703 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.105
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.346 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT793_ALERT_4_G Model has Chirality at C12         (Centro SPGR)          R Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.17 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

(2,2'-Bipyridine-κ²N,N')[2-hydroxy-2-(hydroxymethyl-κO)propanedioato-κ²O¹,O³]copper(II)

Crystal data

[Cu(C4H4O6)(C10H8N2)]	Z = 2
Mr = 367.80	F(000) = 374
Triclinic, P1	Dx = 1.850 Mg m^−3
a = 7.6516 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9272 (6) Å	Cell parameters from 3354 reflections
c = 10.0722 (6) Å	θ = 2.2–29.3°
α = 95.204 (4)°	µ = 1.69 mm^−1
β = 107.729 (4)°	T = 90 K
γ = 111.462 (4)°	Fragment, light blue
V = 660.34 (7) Å^3	0.15 × 0.09 × 0.07 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer	4041 independent reflections
Radiation source: fine-focus sealed tube	2675 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.063
φ and ω scans	θmax = 30.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.838, Tmax = 0.891	k = −14→14
18442 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: mixed
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0436P)^2 + 0.3982P] where P = (Fo^2 + 2Fc^2)/3
4041 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.74 e Å^−3
2 restraints	Δρmin = −0.56 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.60628 (6)	0.63056 (4)	0.41304 (4)	0.01841 (12)
O1	0.7261 (3)	0.5158 (2)	0.52799 (19)	0.0200 (5)
O2	0.9188 (3)	0.7153 (3)	0.3763 (2)	0.0247 (5)
H2O	0.931 (6)	0.635 (3)	0.346 (4)	0.037*
O3	0.7221 (3)	0.7944 (2)	0.5778 (2)	0.0241 (5)
O4	0.9916 (3)	0.5149 (2)	0.6990 (2)	0.0239 (5)
O5	1.2089 (3)	0.8062 (3)	0.7594 (2)	0.0296 (5)
H5O	1.178 (6)	0.869 (4)	0.813 (3)	0.044*
O6	0.9741 (4)	0.9263 (3)	0.7840 (2)	0.0337 (6)
N1	0.4537 (4)	0.7282 (3)	0.2933 (2)	0.0170 (5)
N2	0.4699 (4)	0.4750 (3)	0.2317 (2)	0.0166 (5)
C1	0.4522 (5)	0.8585 (3)	0.3373 (3)	0.0201 (6)
H1	0.5308	0.9116	0.4337	0.024*
C2	0.3410 (5)	0.9188 (3)	0.2483 (3)	0.0217 (7)
H2	0.3409	1.0109	0.2833	0.026*
C3	0.2293 (4)	0.8435 (3)	0.1071 (3)	0.0195 (6)
H3	0.1527	0.8836	0.0433	0.023*
C4	0.2309 (4)	0.7080 (3)	0.0597 (3)	0.0180 (6)
H4	0.1567	0.6548	−0.0372	0.022*
C5	0.3422 (4)	0.6519 (3)	0.1558 (3)	0.0142 (6)
C6	0.3512 (4)	0.5078 (3)	0.1208 (3)	0.0142 (6)
C7	0.2500 (4)	0.4119 (3)	−0.0127 (3)	0.0155 (6)
H7	0.1676	0.4365	−0.0892	0.019*
C8	0.2703 (4)	0.2792 (3)	−0.0335 (3)	0.0180 (6)
H8	0.2000	0.2107	−0.1239	0.022*
C9	0.3938 (5)	0.2480 (3)	0.0789 (3)	0.0191 (6)
H9	0.4109	0.1583	0.0665	0.023*
C10	0.4924 (4)	0.3482 (3)	0.2098 (3)	0.0180 (6)
H10	0.5788	0.3267	0.2866	0.022*
C11	0.9051 (5)	0.5800 (3)	0.6238 (3)	0.0217 (7)
C12	1.0222 (5)	0.7493 (4)	0.6426 (3)	0.0247 (7)
C13	0.8962 (5)	0.8297 (4)	0.6718 (3)	0.0258 (7)
C14	1.0784 (5)	0.7878 (4)	0.5103 (3)	0.0284 (7)
H14A	1.1263	0.8965	0.5195	0.034*
H14B	1.1917	0.7614	0.5117	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0245 (2)	0.0195 (2)	0.00897 (15)	0.01379 (17)	−0.00134 (13)	−0.00131 (13)
O1	0.0255 (12)	0.0221 (12)	0.0104 (9)	0.0137 (10)	−0.0002 (8)	0.0018 (8)
O2	0.0272 (12)	0.0276 (13)	0.0172 (10)	0.0135 (11)	0.0035 (9)	0.0032 (9)
O3	0.0257 (12)	0.0268 (13)	0.0147 (10)	0.0143 (11)	−0.0012 (9)	−0.0040 (9)
O4	0.0247 (12)	0.0272 (12)	0.0202 (10)	0.0155 (10)	0.0031 (9)	0.0053 (9)
O5	0.0283 (13)	0.0337 (14)	0.0213 (11)	0.0169 (11)	−0.0006 (9)	−0.0024 (10)
O6	0.0366 (14)	0.0325 (14)	0.0221 (11)	0.0185 (12)	−0.0035 (10)	−0.0070 (10)
N1	0.0182 (13)	0.0181 (13)	0.0128 (10)	0.0084 (11)	0.0030 (9)	0.0005 (10)
N2	0.0212 (13)	0.0163 (13)	0.0129 (11)	0.0104 (11)	0.0045 (10)	0.0013 (10)
C1	0.0244 (17)	0.0168 (15)	0.0183 (13)	0.0108 (13)	0.0051 (12)	−0.0005 (12)
C2	0.0279 (18)	0.0163 (16)	0.0237 (15)	0.0138 (14)	0.0079 (13)	0.0037 (12)
C3	0.0195 (16)	0.0195 (16)	0.0223 (14)	0.0123 (13)	0.0052 (12)	0.0071 (12)
C4	0.0149 (15)	0.0242 (17)	0.0143 (13)	0.0095 (13)	0.0034 (11)	0.0031 (12)
C5	0.0136 (14)	0.0142 (14)	0.0145 (12)	0.0063 (12)	0.0046 (10)	0.0005 (11)
C6	0.0125 (14)	0.0167 (15)	0.0113 (12)	0.0060 (12)	0.0022 (10)	0.0019 (11)
C7	0.0116 (14)	0.0165 (15)	0.0140 (12)	0.0038 (12)	0.0020 (10)	0.0005 (11)
C8	0.0173 (15)	0.0170 (15)	0.0142 (12)	0.0039 (12)	0.0040 (11)	−0.0016 (11)
C9	0.0241 (16)	0.0142 (15)	0.0214 (14)	0.0101 (13)	0.0092 (12)	0.0022 (12)
C10	0.0202 (16)	0.0201 (16)	0.0155 (13)	0.0108 (13)	0.0056 (11)	0.0044 (12)
C11	0.0310 (18)	0.0229 (17)	0.0115 (12)	0.0158 (15)	0.0035 (12)	0.0006 (12)
C12	0.0257 (17)	0.0276 (18)	0.0162 (13)	0.0123 (15)	0.0010 (12)	0.0019 (13)
C13	0.0288 (18)	0.0260 (18)	0.0209 (15)	0.0149 (15)	0.0036 (13)	0.0015 (14)
C14	0.0271 (18)	0.0294 (19)	0.0235 (15)	0.0108 (16)	0.0049 (13)	0.0008 (14)

Geometric parameters (Å, º)

Cu1—O3	1.935 (2)	C2—H2	0.9500
Cu1—O1	1.9587 (19)	C3—C4	1.391 (4)
Cu1—N1	1.985 (2)	C3—H3	0.9500
Cu1—N2	1.990 (2)	C4—C5	1.383 (4)
Cu1—O2	2.384 (2)	C4—H4	0.9500
O1—C11	1.288 (3)	C5—C6	1.474 (4)
O2—C14	1.417 (4)	C6—C7	1.381 (4)
O2—H2O	0.880 (18)	C7—C8	1.387 (4)
O3—C13	1.275 (4)	C7—H7	0.9500
O4—C11	1.236 (3)	C8—C9	1.377 (4)
O5—C12	1.417 (4)	C8—H8	0.9500
O5—H5O	0.929 (18)	C9—C10	1.380 (4)
O6—C13	1.236 (4)	C9—H9	0.9500
N1—C1	1.334 (4)	C10—H10	0.9500
N1—C5	1.355 (3)	C11—C12	1.549 (5)
N2—C10	1.339 (4)	C12—C13	1.532 (4)
N2—C6	1.358 (3)	C12—C14	1.558 (4)
C1—C2	1.375 (4)	C14—H14A	0.9900
C1—H1	0.9500	C14—H14B	0.9900
C2—C3	1.383 (4)
O3—Cu1—O1	91.06 (8)	N1—C5—C6	114.2 (2)
O3—Cu1—N1	91.97 (9)	C4—C5—C6	124.4 (2)
O1—Cu1—N1	173.29 (10)	N2—C6—C7	121.5 (3)
O3—Cu1—N2	173.32 (9)	N2—C6—C5	114.4 (2)
O1—Cu1—N2	95.56 (9)	C7—C6—C5	124.1 (2)
N1—Cu1—N2	81.35 (9)	C6—C7—C8	119.1 (3)
O3—Cu1—O2	90.05 (9)	C6—C7—H7	120.4
O1—Cu1—O2	81.94 (8)	C8—C7—H7	120.4
N1—Cu1—O2	104.04 (9)	C9—C8—C7	119.0 (3)
N2—Cu1—O2	91.77 (9)	C9—C8—H8	120.5
C11—O1—Cu1	120.61 (19)	C7—C8—H8	120.5
C14—O2—Cu1	108.93 (18)	C8—C9—C10	119.5 (3)
C14—O2—H2O	106 (2)	C8—C9—H9	120.3
Cu1—O2—H2O	106 (2)	C10—C9—H9	120.3
C13—O3—Cu1	121.7 (2)	N2—C10—C9	121.9 (3)
C12—O5—H5O	96 (2)	N2—C10—H10	119.1
C1—N1—C5	119.1 (2)	C9—C10—H10	119.1
C1—N1—Cu1	125.71 (19)	O4—C11—O1	124.3 (3)
C5—N1—Cu1	115.18 (19)	O4—C11—C12	117.9 (3)
C10—N2—C6	119.0 (2)	O1—C11—C12	117.8 (2)
C10—N2—Cu1	126.08 (19)	O5—C12—C13	108.3 (2)
C6—N2—Cu1	114.81 (18)	O5—C12—C11	111.3 (2)
N1—C1—C2	122.5 (3)	C13—C12—C11	109.2 (3)
N1—C1—H1	118.8	O5—C12—C14	105.0 (3)
C2—C1—H1	118.8	C13—C12—C14	110.5 (3)
C1—C2—C3	119.0 (3)	C11—C12—C14	112.4 (2)
C1—C2—H2	120.5	O6—C13—O3	125.2 (3)
C3—C2—H2	120.5	O6—C13—C12	117.0 (3)
C2—C3—C4	119.0 (3)	O3—C13—C12	117.8 (3)
C2—C3—H3	120.5	O2—C14—C12	114.7 (3)
C4—C3—H3	120.5	O2—C14—H14A	108.6
C5—C4—C3	119.0 (3)	C12—C14—H14A	108.6
C5—C4—H4	120.5	O2—C14—H14B	108.6
C3—C4—H4	120.5	C12—C14—H14B	108.6
N1—C5—C4	121.4 (3)	H14A—C14—H14B	107.6
C5—N1—C1—C2	0.1 (5)	C6—N2—C10—C9	−2.0 (4)
Cu1—N1—C1—C2	−179.4 (2)	Cu1—N2—C10—C9	−178.8 (2)
N1—C1—C2—C3	−1.3 (5)	C8—C9—C10—N2	0.8 (5)
C1—C2—C3—C4	0.8 (5)	Cu1—O1—C11—O4	−179.0 (2)
C2—C3—C4—C5	0.8 (4)	Cu1—O1—C11—C12	−1.0 (4)
C1—N1—C5—C4	1.5 (4)	O4—C11—C12—O5	−6.9 (4)
Cu1—N1—C5—C4	−178.9 (2)	O1—C11—C12—O5	175.0 (2)
C1—N1—C5—C6	−178.4 (3)	O4—C11—C12—C13	−126.3 (3)
Cu1—N1—C5—C6	1.2 (3)	O1—C11—C12—C13	55.6 (3)
C3—C4—C5—N1	−2.0 (4)	O4—C11—C12—C14	110.7 (3)
C3—C4—C5—C6	177.9 (3)	O1—C11—C12—C14	−67.4 (4)
C10—N2—C6—C7	1.6 (4)	Cu1—O3—C13—O6	−175.1 (3)
Cu1—N2—C6—C7	178.7 (2)	Cu1—O3—C13—C12	6.5 (4)
C10—N2—C6—C5	−178.2 (3)	O5—C12—C13—O6	1.0 (4)
Cu1—N2—C6—C5	−1.1 (3)	C11—C12—C13—O6	122.3 (3)
N1—C5—C6—N2	−0.1 (4)	C14—C12—C13—O6	−113.5 (3)
C4—C5—C6—N2	−179.9 (3)	O5—C12—C13—O3	179.6 (3)
N1—C5—C6—C7	−179.9 (3)	C11—C12—C13—O3	−59.1 (4)
C4—C5—C6—C7	0.3 (5)	C14—C12—C13—O3	65.1 (4)
N2—C6—C7—C8	0.0 (4)	Cu1—O2—C14—C12	19.3 (3)
C5—C6—C7—C8	179.8 (3)	O5—C12—C14—O2	167.8 (3)
C6—C7—C8—C9	−1.2 (4)	C13—C12—C14—O2	−75.7 (3)
C7—C8—C9—C10	0.8 (4)	C11—C12—C14—O2	46.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O4^i	0.88 (2)	1.85 (2)	2.723 (3)	169 (4)
O5—H5O···O6	0.93 (2)	1.80 (3)	2.549 (3)	136 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.