[N,N′-Bis(1-{[2-oxido-4-(2-hydroxy­ethoxy)­phenyl]­methyl}ethyl­idene)­ethane-1,2-di­amine]copper(II)

In the title complex, [Cu(C₂₂H₂₆N₂O₆)], the coordination geometry about the Cu atom is a 6–5–6 chelate ring structure with a tetrahedrally distorted square plane formed by the four-coordinate N₂O₂ donor set of the Schiff base imine–phenol ligand. The crystal packing is stabilized by intermolecular O—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.108
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Alert level B
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H10C   ..  H11B    ..       1.78 Ang.

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           27.99
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               4633
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5091
           Completeness (_total/calc)             91.00%

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

[N,N'-Bis(1-{[2-oxido-4-(2-hydroxyethoxy)phenyl]methyl}ethylidene)ethane- 1,2-diamine]copper(II)

Crystal data

[Cu(C22H26N2O6)]	F(000) = 996
Mr = 477.99	Dx = 1.505 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4421 reflections
a = 11.8535 (7) Å	θ = 2.4–27.2°
b = 8.6424 (5) Å	µ = 1.08 mm^−1
c = 21.0047 (13) Å	T = 293 K
β = 101.451 (1)°	Block, red
V = 2108.9 (2) Å^3	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection

CCD Aread Detector diffractometer	3861 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 28.0°, θmin = 1.8°
ω scans	h = −15→15
12545 measured reflections	k = −11→10
4633 independent reflections	l = −27→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 0.3364P] where P = (Fo^2 + 2Fc^2)/3
4633 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.66442 (2)	0.90832 (3)	0.012539 (13)	0.02912 (10)
O3	0.59352 (13)	0.78568 (18)	0.06756 (7)	0.0356 (4)
N2	0.74827 (16)	1.0227 (2)	−0.04260 (9)	0.0337 (4)
O2	0.32000 (14)	0.4692 (2)	0.14096 (8)	0.0428 (4)
O6	1.24551 (14)	1.1275 (2)	0.34100 (8)	0.0407 (4)
H6	1.2865	1.1709	0.3719	0.061*
O5	1.06829 (13)	1.20756 (19)	0.23378 (8)	0.0414 (4)
N1	0.55310 (15)	0.8545 (2)	−0.06422 (9)	0.0302 (4)
C6	0.43390 (17)	0.6888 (2)	−0.01277 (11)	0.0294 (4)
C15	0.89045 (18)	1.1376 (3)	0.04227 (11)	0.0325 (5)
O4	0.76989 (14)	0.9605 (2)	0.08786 (8)	0.0467 (4)
C9	0.46362 (17)	0.7639 (2)	−0.06943 (11)	0.0292 (4)
C19	0.91626 (19)	1.0816 (3)	0.15816 (12)	0.0368 (5)
H19	0.8943	1.0269	0.1918	0.044*
C7	0.49759 (17)	0.7058 (2)	0.05142 (11)	0.0287 (4)
O1	0.34704 (17)	0.2430 (2)	0.24268 (9)	0.0532 (5)
H1	0.3120	0.1889	0.2643	0.080*
C1	0.3189 (2)	0.3999 (3)	0.24973 (12)	0.0416 (6)
H1A	0.3442	0.4315	0.2946	0.050*
H1B	0.2362	0.4136	0.2380	0.050*
C20	0.85558 (18)	1.0586 (2)	0.09422 (12)	0.0333 (5)
C8	0.45888 (18)	0.6341 (2)	0.10316 (11)	0.0327 (5)
H8	0.4999	0.6483	0.1453	0.039*
C21	1.0517 (2)	1.1002 (3)	0.28285 (13)	0.0453 (6)
H21A	1.0699	0.9962	0.2707	0.054*
H21B	0.9720	1.1020	0.2877	0.054*
C2	0.3765 (2)	0.4966 (3)	0.20676 (11)	0.0437 (6)
H2A	0.3712	0.6052	0.2174	0.052*
H2B	0.4573	0.4690	0.2127	0.052*
C3	0.36158 (18)	0.5431 (2)	0.09285 (11)	0.0328 (5)
C18	1.00704 (18)	1.1827 (2)	0.17217 (12)	0.0342 (5)
C17	1.0401 (2)	1.2659 (3)	0.12217 (12)	0.0412 (6)
H17	1.1002	1.3367	0.1312	0.049*
C11	0.5761 (2)	0.9410 (3)	−0.12052 (11)	0.0358 (5)
H11A	0.5297	1.0343	−0.1264	0.043*
H11B	0.5548	0.8784	−0.1594	0.043*
C16	0.9836 (2)	1.2425 (3)	0.05989 (12)	0.0409 (6)
H16	1.0073	1.2983	0.0271	0.049*
C5	0.33464 (18)	0.5934 (3)	−0.02053 (12)	0.0364 (5)
H5	0.2913	0.5792	−0.0621	0.044*
C14	0.8947 (2)	1.1811 (3)	−0.07770 (12)	0.0481 (6)
H14A	0.8950	1.1072	−0.1118	0.072*
H14B	0.9723	1.2103	−0.0590	0.072*
H14C	0.8520	1.2711	−0.0952	0.072*
C4	0.29978 (18)	0.5216 (3)	0.03012 (12)	0.0374 (5)
H4	0.2349	0.4585	0.0226	0.045*
C12	0.7020 (2)	0.9836 (3)	−0.11093 (11)	0.0431 (6)
H12A	0.7448	0.8975	−0.1238	0.052*
H12B	0.7110	1.0714	−0.1382	0.052*
C13	0.83895 (18)	1.1099 (3)	−0.02585 (12)	0.0330 (5)
C10	0.3866 (2)	0.7380 (3)	−0.13453 (12)	0.0435 (6)
H10A	0.3196	0.8023	−0.1384	0.065*
H10B	0.3637	0.6313	−0.1385	0.065*
H10C	0.4274	0.7637	−0.1683	0.065*
C22	1.1289 (2)	1.1452 (3)	0.34539 (12)	0.0429 (6)
H22A	1.1145	1.2521	0.3554	0.052*
H22B	1.1124	1.0810	0.3803	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.02965 (16)	0.03492 (16)	0.02126 (17)	−0.00151 (9)	0.00140 (12)	0.00043 (10)
O3	0.0348 (8)	0.0447 (9)	0.0238 (8)	−0.0117 (6)	−0.0024 (7)	0.0031 (7)
N2	0.0358 (9)	0.0421 (10)	0.0232 (10)	0.0011 (8)	0.0056 (8)	0.0009 (8)
O2	0.0404 (9)	0.0591 (10)	0.0275 (9)	−0.0199 (8)	0.0036 (8)	−0.0032 (8)
O6	0.0370 (8)	0.0518 (10)	0.0294 (10)	−0.0025 (7)	−0.0027 (7)	−0.0016 (7)
O5	0.0391 (8)	0.0478 (9)	0.0322 (10)	−0.0137 (7)	−0.0050 (8)	0.0038 (7)
N1	0.0342 (9)	0.0330 (9)	0.0215 (10)	0.0041 (7)	0.0009 (8)	−0.0022 (7)
C6	0.0308 (10)	0.0289 (10)	0.0254 (12)	0.0029 (8)	−0.0015 (9)	−0.0043 (8)
C15	0.0293 (10)	0.0377 (11)	0.0295 (13)	0.0025 (8)	0.0031 (10)	0.0031 (9)
O4	0.0423 (9)	0.0662 (11)	0.0272 (10)	−0.0244 (8)	−0.0035 (8)	0.0082 (8)
C9	0.0312 (10)	0.0302 (10)	0.0230 (11)	0.0072 (8)	−0.0026 (9)	−0.0036 (8)
C19	0.0313 (11)	0.0484 (13)	0.0293 (13)	−0.0075 (9)	0.0030 (10)	0.0034 (10)
C7	0.0278 (9)	0.0297 (10)	0.0268 (12)	0.0015 (7)	0.0009 (9)	−0.0015 (8)
O1	0.0689 (13)	0.0542 (11)	0.0426 (12)	−0.0006 (9)	0.0263 (10)	−0.0005 (9)
C1	0.0419 (13)	0.0554 (15)	0.0292 (14)	−0.0126 (10)	0.0113 (11)	−0.0103 (11)
C20	0.0287 (10)	0.0398 (12)	0.0302 (13)	−0.0030 (8)	0.0029 (10)	0.0019 (9)
C8	0.0319 (11)	0.0374 (11)	0.0257 (12)	−0.0031 (8)	−0.0019 (9)	−0.0032 (9)
C21	0.0421 (13)	0.0551 (15)	0.0339 (15)	−0.0160 (10)	−0.0037 (12)	0.0058 (11)
C2	0.0445 (13)	0.0553 (15)	0.0317 (14)	−0.0175 (11)	0.0089 (11)	−0.0088 (11)
C3	0.0299 (10)	0.0369 (11)	0.0309 (13)	−0.0023 (8)	0.0045 (10)	−0.0031 (9)
C18	0.0293 (10)	0.0374 (11)	0.0334 (13)	−0.0018 (8)	−0.0003 (10)	0.0007 (10)
C17	0.0363 (12)	0.0424 (13)	0.0422 (16)	−0.0108 (9)	0.0010 (11)	0.0047 (11)
C11	0.0445 (13)	0.0405 (12)	0.0202 (12)	0.0009 (9)	0.0009 (10)	0.0004 (9)
C16	0.0398 (12)	0.0450 (13)	0.0374 (15)	−0.0070 (10)	0.0065 (11)	0.0095 (11)
C5	0.0314 (11)	0.0448 (13)	0.0280 (14)	0.0000 (9)	−0.0059 (10)	−0.0067 (10)
C14	0.0475 (14)	0.0653 (17)	0.0341 (15)	−0.0074 (12)	0.0144 (12)	0.0046 (12)
C4	0.0301 (11)	0.0452 (12)	0.0344 (14)	−0.0082 (9)	0.0008 (10)	−0.0065 (10)
C12	0.0455 (13)	0.0608 (15)	0.0230 (13)	−0.0022 (11)	0.0071 (11)	−0.0007 (11)
C13	0.0333 (11)	0.0371 (11)	0.0305 (13)	0.0048 (8)	0.0109 (10)	0.0041 (9)
C10	0.0455 (13)	0.0504 (14)	0.0284 (14)	−0.0070 (10)	−0.0078 (11)	0.0034 (11)
C22	0.0388 (12)	0.0561 (14)	0.0313 (14)	−0.0096 (10)	0.0005 (11)	−0.0003 (11)

Geometric parameters (Å, º)

Cu1—O4	1.867 (2)	C1—H1B	0.9700
Cu1—O3	1.885 (2)	C8—C3	1.377 (3)
Cu1—N1	1.927 (2)	C8—H8	0.9300
Cu1—N2	1.940 (2)	C21—C22	1.496 (3)
O3—C7	1.316 (2)	C21—H21A	0.9700
N2—C13	1.302 (3)	C21—H21B	0.9700
N2—C12	1.471 (3)	C2—H2A	0.9700
O2—C3	1.368 (3)	C2—H2B	0.9700
O2—C2	1.431 (3)	C3—C4	1.387 (3)
O6—C22	1.411 (3)	C18—C17	1.391 (3)
O6—H6	0.8200	C17—C16	1.361 (3)
O5—C18	1.369 (3)	C17—H17	0.9300
O5—C21	1.429 (3)	C11—C12	1.511 (3)
N1—C9	1.306 (3)	C11—H11A	0.9700
N1—C11	1.469 (3)	C11—H11B	0.9700
C6—C7	1.416 (3)	C16—H16	0.9300
C6—C5	1.419 (3)	C5—C4	1.365 (3)
C6—C9	1.459 (3)	C5—H5	0.9300
C15—C20	1.417 (3)	C14—C13	1.512 (3)
C15—C16	1.420 (3)	C14—H14A	0.9600
C15—C13	1.460 (3)	C14—H14B	0.9600
O4—C20	1.309 (3)	C14—H14C	0.9600
C9—C10	1.502 (3)	C4—H4	0.9300
C19—C18	1.372 (3)	C12—H12A	0.9700
C19—C20	1.406 (3)	C12—H12B	0.9700
C19—H19	0.9300	C10—H10A	0.9600
C7—C8	1.405 (3)	C10—H10B	0.9600
O1—C1	1.410 (3)	C10—H10C	0.9600
O1—H1	0.8200	C22—H22A	0.9700
C1—C2	1.492 (3)	C22—H22B	0.9700
C1—H1A	0.9700
O4—Cu1—O3	85.5 (1)	O2—C2—H2B	110.1
O4—Cu1—N1	178.8 (1)	C1—C2—H2B	110.1
O3—Cu1—N1	93.6 (1)	H2A—C2—H2B	108.4
O4—Cu1—N2	92.7 (1)	O2—C3—C8	124.3 (2)
O3—Cu1—N2	175.2 (1)	O2—C3—C4	116.07 (19)
N1—Cu1—N2	88.3 (1)	C8—C3—C4	119.6 (2)
C7—O3—Cu1	127.22 (14)	O5—C18—C19	123.3 (2)
C13—N2—C12	121.65 (19)	O5—C18—C17	117.16 (19)
C13—N2—Cu1	128.80 (16)	C19—C18—C17	119.6 (2)
C12—N2—Cu1	109.23 (14)	C16—C17—C18	119.4 (2)
C3—O2—C2	117.92 (17)	C16—C17—H17	120.3
C22—O6—H6	109.5	C18—C17—H17	120.3
C18—O5—C21	117.17 (17)	N1—C11—C12	110.67 (19)
C9—N1—C11	121.01 (19)	N1—C11—H11A	109.5
C9—N1—Cu1	128.68 (16)	C12—C11—H11A	109.5
C11—N1—Cu1	110.18 (14)	N1—C11—H11B	109.5
C7—C6—C5	116.3 (2)	C12—C11—H11B	109.5
C7—C6—C9	124.13 (19)	H11A—C11—H11B	108.1
C5—C6—C9	119.6 (2)	C17—C16—C15	123.7 (2)
C20—C15—C16	116.0 (2)	C17—C16—H16	118.2
C20—C15—C13	123.2 (2)	C15—C16—H16	118.2
C16—C15—C13	120.8 (2)	C4—C5—C6	123.2 (2)
C20—O4—Cu1	128.21 (16)	C4—C5—H5	118.4
N1—C9—C6	121.5 (2)	C6—C5—H5	118.4
N1—C9—C10	120.2 (2)	C13—C14—H14A	109.5
C6—C9—C10	118.33 (19)	C13—C14—H14B	109.5
C18—C19—C20	121.7 (2)	H14A—C14—H14B	109.5
C18—C19—H19	119.1	C13—C14—H14C	109.5
C20—C19—H19	119.1	H14A—C14—H14C	109.5
O3—C7—C8	115.49 (19)	H14B—C14—H14C	109.5
O3—C7—C6	124.7 (2)	C5—C4—C3	119.7 (2)
C8—C7—C6	119.77 (19)	C5—C4—H4	120.2
C1—O1—H1	109.5	C3—C4—H4	120.2
O1—C1—C2	109.2 (2)	N2—C12—C11	110.70 (18)
O1—C1—H1A	109.8	N2—C12—H12A	109.5
C2—C1—H1A	109.8	C11—C12—H12A	109.5
O1—C1—H1B	109.8	N2—C12—H12B	109.5
C2—C1—H1B	109.8	C11—C12—H12B	109.5
H1A—C1—H1B	108.3	H12A—C12—H12B	108.1
O4—C20—C19	115.4 (2)	N2—C13—C15	121.5 (2)
O4—C20—C15	124.9 (2)	N2—C13—C14	119.7 (2)
C19—C20—C15	119.7 (2)	C15—C13—C14	118.8 (2)
C3—C8—C7	121.5 (2)	C9—C10—H10A	109.5
C3—C8—H8	119.3	C9—C10—H10B	109.5
C7—C8—H8	119.3	H10A—C10—H10B	109.5
O5—C21—C22	108.45 (19)	C9—C10—H10C	109.5
O5—C21—H21A	110.0	H10A—C10—H10C	109.5
C22—C21—H21A	110.0	H10B—C10—H10C	109.5
O5—C21—H21B	110.0	O6—C22—C21	110.5 (2)
C22—C21—H21B	110.0	O6—C22—H22A	109.5
H21A—C21—H21B	108.4	C21—C22—H22A	109.5
O2—C2—C1	108.00 (18)	O6—C22—H22B	109.5
O2—C2—H2A	110.1	C21—C22—H22B	109.5
C1—C2—H2A	110.1	H22A—C22—H22B	108.1
O4—Cu1—O3—C7	175.98 (18)	C18—O5—C21—C22	178.13 (19)
N1—Cu1—O3—C7	−3.31 (18)	C3—O2—C2—C1	−178.0 (2)
O4—Cu1—N2—C13	−4.7 (2)	O1—C1—C2—O2	71.4 (3)
N1—Cu1—N2—C13	174.6 (2)	C2—O2—C3—C8	4.5 (3)
O4—Cu1—N2—C12	168.68 (16)	C2—O2—C3—C4	−175.9 (2)
N1—Cu1—N2—C12	−11.96 (15)	C7—C8—C3—O2	179.4 (2)
O3—Cu1—N1—C9	0.24 (18)	C7—C8—C3—C4	−0.2 (3)
N2—Cu1—N1—C9	175.83 (18)	C21—O5—C18—C19	13.3 (3)
O3—Cu1—N1—C11	176.09 (14)	C21—O5—C18—C17	−166.9 (2)
N2—Cu1—N1—C11	−8.33 (14)	C20—C19—C18—O5	−179.7 (2)
O3—Cu1—O4—C20	−176.2 (2)	C20—C19—C18—C17	0.4 (3)
N2—Cu1—O4—C20	8.2 (2)	O5—C18—C17—C16	178.5 (2)
C11—N1—C9—C6	−174.21 (17)	C19—C18—C17—C16	−1.7 (3)
Cu1—N1—C9—C6	1.2 (3)	C9—N1—C11—C12	−157.3 (2)
C11—N1—C9—C10	4.2 (3)	Cu1—N1—C11—C12	26.5 (2)
Cu1—N1—C9—C10	179.64 (15)	C18—C17—C16—C15	0.6 (4)
C7—C6—C9—N1	−0.3 (3)	C20—C15—C16—C17	1.7 (3)
C5—C6—C9—N1	178.83 (19)	C13—C15—C16—C17	−175.6 (2)
C7—C6—C9—C10	−178.7 (2)	C7—C6—C5—C4	0.5 (3)
C5—C6—C9—C10	0.4 (3)	C9—C6—C5—C4	−178.7 (2)
Cu1—O3—C7—C8	−175.07 (14)	C6—C5—C4—C3	1.3 (3)
Cu1—O3—C7—C6	5.0 (3)	O2—C3—C4—C5	179.0 (2)
C5—C6—C7—O3	177.90 (19)	C8—C3—C4—C5	−1.4 (3)
C9—C6—C7—O3	−2.9 (3)	C13—N2—C12—C11	−156.8 (2)
C5—C6—C7—C8	−2.1 (3)	Cu1—N2—C12—C11	29.3 (2)
C9—C6—C7—C8	177.11 (18)	N1—C11—C12—N2	−36.9 (3)
Cu1—O4—C20—C19	176.01 (16)	C12—N2—C13—C15	−174.7 (2)
Cu1—O4—C20—C15	−5.1 (3)	Cu1—N2—C13—C15	−2.0 (3)
C18—C19—C20—O4	−179.1 (2)	C12—N2—C13—C14	3.7 (3)
C18—C19—C20—C15	2.0 (3)	Cu1—N2—C13—C14	176.38 (16)
C16—C15—C20—O4	178.2 (2)	C20—C15—C13—N2	8.0 (3)
C13—C15—C20—O4	−4.5 (4)	C16—C15—C13—N2	−174.9 (2)
C16—C15—C20—C19	−2.9 (3)	C20—C15—C13—C14	−170.4 (2)
C13—C15—C20—C19	174.3 (2)	C16—C15—C13—C14	6.7 (3)
O3—C7—C8—C3	−178.01 (19)	O5—C21—C22—O6	−65.8 (3)
C6—C7—C8—C3	1.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O1^i	0.97	2.52	3.297 (3)	138
O1—H1···O6^ii	0.82	2.00	2.775 (2)	157
O6—H6···O3^iii	0.82	1.98	2.783 (2)	168
C22—H22A···O4^iii	0.97	2.43	3.188 (3)	135

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