cis-[N-(4-Chloro­benz­yl)imino­diacetato-κ3N,O,O′]bis­(1H-imidazole-κN3)copper(II)

Brandi-Blanco, M.P.; Benavides-Giménez, M.M. de; González-Pérez, J.M.; Choquesillo-Lazarte, D.

doi:10.1107/S160053680702288X

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cis-[N-(4-Chlorobenzyl)iminodiacetato-κ³N,O,O′]bis(1H-imidazole-κN³)copper(II)

M. P. Brandi-Blanco, M. M. de Benavides-Giménez, J. M. González-Pérez and D. Choquesillo-Lazarte

In the title compound, [Cu(C₁₁H₁₀ClNO₄)(C₃H₄N)₂], the Cu^II atom is in a square-pyramidal coordination geometry, with the two imidazole ligands in cis positions and the N-(4-chlorobenzyl)iminodiacetate ligand occupying the apical and two cis-basal positions. In the crystal structure, molecules are linked into sheets by N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702288X/pr2009sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702288X/pr2009Isup2.hkl Contains datablock I

CCDC reference: 650681

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.032
wR factor = 0.086
Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.14

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The molecular structure of (I) (Fig. 1) is centrosymmetric. The Cu(II) atom exhibits a square pyramidal coordination geometry, with a τ parameter of 0.27 (Addison et al., 1984), built by a N-(p-chlorobenzyl)iminodiacetato ligand in a fac-tridentate conformation and two cis imidazole ligands. In the dianionic ligand, the two five-membered chelate rings lie nearly perpendicular (dihedral angle 72.1 (1)°).

In the crystal, centrosymmetric pairs of molecules are H-bonded by two N—H···O interactions involving parallel Him (N23) ligands which are weakly π,π-stacked (Fig. 2). Additional N—H···O interactions connect pairs of molecules generating sheets (Fig. 3).

Related literature top

In addition to the related dinuclear iminodiacetate derivative (Nguyen-Huy et al., 1990), it is known that a closely related N-(benzyl)iminodiacetate(2-) derivative also exists, and is a Him solvate as well, with Him referring to the imidazole molecule (Polyakova et al., 2001).

For related literature, see: Addison et al. (1984).

Experimental top

The new ternary complex [Cu^II(C₁₁H₁₀ClNO₄)(C₃H₄N)₂] was obtained by reaction of a mixture having Cu₂CO₃(OH)₂/H₂L/Him 1 mmol/2 mmol/20 mmol (H₂L, N-(p-chlorobenzyl)iminodiacetic acid; Him, imidazole) in water (200 ml); with Him in a large excess. The resulting solution was filtered on a crystallization device which was covered with a plastic film to control the evaporation. After multiple days, prismatic blue crystals were collected and used for X-ray diffraction studies.

Structure description top

For related literature, see: Addison et al. (1984).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

	Fig. 1. A view of the asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as spheres of arbitrary radii.
	Fig. 2. A pair of centrosymmetric molecules of (I) built by N—H···O and π,π-interactions (dashed lines). Symmetry code (i): -x, -y, -z.
	Fig. 3. A view of part of the crystal structure of (I), showing the formation of a sheet. The hydrogen bonds and π,π stacking interactions are shown as dashed lines and for the sake of clarity the H atoms bonded to C atoms have been omitted..

cis-[N-(4-Chlorobenzyl)iminodiacetato-κ³N,O,O']bis(1H-imidazole- κN³)copper(II) top

Crystal data top

[Cu(C₁₁H₁₀ClNO₄)(C₃H₄N)₂]	F(000) = 932
M_r = 455.35	D_x = 1.599 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9904 reflections
a = 10.2028 (5) Å	θ = 2.3–27.8°
b = 13.4280 (6) Å	µ = 1.33 mm⁻¹
c = 13.9113 (7) Å	T = 298 K
β = 97.119 (1)°	Prism, blue
V = 1891.20 (16) Å³	0.49 × 0.32 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4437 independent reflections
Radiation source: fine-focus sealed tube	4043 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→13
T_min = 0.562, T_max = 0.825	k = −17→17
21629 measured reflections	l = −18→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0462P)² + 0.8491P] where P = (F_o² + 2F_c²)/3
4437 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu(C₁₁H₁₀ClNO₄)(C₃H₄N)₂]	V = 1891.20 (16) Å³
M_r = 455.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2028 (5) Å	µ = 1.33 mm⁻¹
b = 13.4280 (6) Å	T = 298 K
c = 13.9113 (7) Å	0.49 × 0.32 × 0.15 mm
β = 97.119 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4437 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4043 reflections with I > 2σ(I)
T_min = 0.562, T_max = 0.825	R_int = 0.024
21629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
4437 reflections	Δρ_min = −0.48 e Å⁻³
253 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	0.245284 (19)	0.061386 (15)	0.202469 (15)	0.02673 (8)
N1	0.42366 (14)	0.13906 (11)	0.21938 (11)	0.0286 (3)
C2	0.39633 (19)	0.24419 (13)	0.19177 (15)	0.0357 (4)
H2A	0.4771	0.2751	0.1764	0.043*
H2B	0.3680	0.2795	0.2464	0.043*
C3	0.28983 (18)	0.25385 (14)	0.10470 (14)	0.0334 (4)
O4	0.20768 (13)	0.18265 (10)	0.09352 (10)	0.0367 (3)
O5	0.28859 (16)	0.33030 (12)	0.05607 (13)	0.0534 (4)
C6	0.49925 (17)	0.09147 (13)	0.14677 (14)	0.0309 (4)
H6A	0.5931	0.0976	0.1682	0.037*
H6B	0.4806	0.1261	0.0854	0.037*
C7	0.46428 (17)	−0.01813 (13)	0.13216 (13)	0.0294 (3)
O8	0.34874 (12)	−0.04288 (9)	0.14890 (10)	0.0340 (3)
O9	0.54492 (13)	−0.07508 (10)	0.10158 (11)	0.0390 (3)
C10	0.4993 (2)	0.13779 (15)	0.31940 (14)	0.0382 (4)
H10A	0.5713	0.1852	0.3219	0.046*
H10B	0.4413	0.1591	0.3656	0.046*
C11	0.55438 (19)	0.03720 (15)	0.34877 (14)	0.0354 (4)
C12	0.4757 (2)	−0.03648 (16)	0.38096 (15)	0.0391 (4)
H12	0.3882	−0.0224	0.3882	0.047*
C13	0.5256 (2)	−0.13117 (17)	0.40257 (15)	0.0429 (5)
H13	0.4726	−0.1808	0.4240	0.052*
C14	0.6554 (2)	−0.14963 (16)	0.39155 (16)	0.0452 (5)
Cl14	0.71813 (8)	−0.26918 (5)	0.41465 (7)	0.0785 (2)
C15	0.7374 (2)	−0.0771 (2)	0.3637 (2)	0.0544 (6)
H15	0.8257	−0.0909	0.3589	0.065*
C16	0.6863 (2)	0.01688 (18)	0.34306 (17)	0.0478 (5)
H16	0.7412	0.0671	0.3251	0.057*
N21	0.08104 (14)	−0.01447 (12)	0.15999 (11)	0.0313 (3)
C22	0.06850 (19)	−0.08136 (14)	0.09012 (14)	0.0342 (4)
H22	0.1385	−0.1074	0.0612	0.041*
N23	−0.05788 (16)	−0.10680 (13)	0.06625 (12)	0.0385 (4)
H23	−0.0938	−0.1400	0.0178	0.046*
C24	−0.1310 (2)	−0.05290 (18)	0.12264 (19)	0.0507 (6)
H24	−0.2223	−0.0544	0.1215	0.061*
C25	−0.0452 (2)	0.00305 (19)	0.18050 (17)	0.0484 (5)
H25	−0.0678	0.0470	0.2274	0.058*
N31	0.16465 (15)	0.12642 (12)	0.31048 (11)	0.0333 (3)
C32	0.1159 (2)	0.21764 (15)	0.30966 (15)	0.0382 (4)
H32	0.1343	0.2672	0.2666	0.046*
N33	0.03733 (18)	0.22961 (13)	0.37816 (13)	0.0432 (4)
H33	0.0069	0.2872	0.3912	0.052*
C34	0.0349 (2)	0.14175 (17)	0.42734 (16)	0.0463 (5)
H34	−0.0118	0.1283	0.4792	0.056*
C35	0.1139 (2)	0.07826 (15)	0.38561 (15)	0.0393 (4)
H35	0.1314	0.0127	0.4045	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02382 (12)	0.02576 (13)	0.03157 (13)	−0.00142 (7)	0.00726 (8)	−0.00333 (8)
N1	0.0274 (7)	0.0249 (7)	0.0333 (7)	−0.0021 (5)	0.0031 (6)	−0.0019 (6)
C2	0.0360 (10)	0.0241 (8)	0.0469 (10)	−0.0043 (7)	0.0046 (8)	−0.0022 (8)
C3	0.0313 (9)	0.0308 (9)	0.0398 (9)	0.0016 (7)	0.0114 (7)	0.0025 (7)
O4	0.0364 (7)	0.0343 (7)	0.0383 (7)	−0.0045 (5)	−0.0003 (5)	0.0031 (6)
O5	0.0478 (9)	0.0449 (9)	0.0683 (10)	−0.0006 (7)	0.0098 (8)	0.0252 (8)
C6	0.0265 (8)	0.0296 (9)	0.0377 (9)	−0.0038 (7)	0.0082 (7)	−0.0015 (7)
C7	0.0255 (8)	0.0314 (9)	0.0316 (8)	−0.0010 (7)	0.0049 (7)	−0.0008 (7)
O8	0.0254 (6)	0.0296 (6)	0.0486 (8)	−0.0038 (5)	0.0113 (5)	−0.0092 (5)
O9	0.0299 (7)	0.0339 (7)	0.0560 (9)	0.0008 (5)	0.0167 (6)	−0.0054 (6)
C10	0.0384 (10)	0.0348 (10)	0.0393 (10)	−0.0033 (8)	−0.0035 (8)	−0.0060 (8)
C11	0.0330 (9)	0.0404 (10)	0.0314 (9)	−0.0022 (8)	−0.0017 (7)	−0.0025 (8)
C12	0.0287 (9)	0.0492 (11)	0.0391 (10)	−0.0023 (8)	0.0026 (8)	0.0010 (9)
C13	0.0398 (11)	0.0451 (11)	0.0428 (11)	−0.0094 (9)	0.0007 (8)	0.0053 (9)
C14	0.0470 (12)	0.0425 (11)	0.0456 (11)	0.0057 (9)	0.0037 (9)	0.0062 (9)
Cl14	0.0848 (5)	0.0506 (4)	0.1031 (6)	0.0214 (3)	0.0231 (4)	0.0204 (4)
C15	0.0358 (11)	0.0629 (15)	0.0663 (15)	0.0110 (10)	0.0133 (10)	0.0200 (12)
C16	0.0341 (10)	0.0507 (13)	0.0582 (13)	−0.0046 (9)	0.0043 (9)	0.0146 (10)
N21	0.0252 (7)	0.0338 (8)	0.0356 (8)	−0.0022 (6)	0.0065 (6)	−0.0010 (6)
C22	0.0328 (9)	0.0332 (9)	0.0370 (9)	−0.0026 (7)	0.0057 (7)	−0.0010 (7)
N23	0.0357 (8)	0.0392 (9)	0.0388 (8)	−0.0086 (7)	−0.0023 (7)	0.0000 (7)
C24	0.0264 (10)	0.0654 (15)	0.0606 (14)	−0.0069 (9)	0.0062 (9)	−0.0075 (11)
C25	0.0275 (10)	0.0648 (15)	0.0548 (13)	−0.0037 (9)	0.0123 (9)	−0.0177 (11)
N31	0.0355 (8)	0.0315 (8)	0.0344 (8)	0.0009 (6)	0.0104 (6)	−0.0024 (6)
C32	0.0446 (11)	0.0333 (10)	0.0388 (10)	0.0050 (8)	0.0130 (8)	0.0007 (8)
N33	0.0490 (10)	0.0373 (9)	0.0459 (9)	0.0095 (8)	0.0169 (8)	−0.0047 (7)
C34	0.0542 (13)	0.0482 (12)	0.0403 (11)	0.0032 (10)	0.0214 (9)	−0.0007 (9)
C35	0.0469 (11)	0.0328 (10)	0.0402 (10)	0.0028 (8)	0.0138 (9)	0.0026 (8)

Geometric parameters (Å, º) top

Cu1—O8	1.9556 (13)	C13—C14	1.374 (3)
Cu1—N21	1.9874 (15)	C13—H13	0.9300
Cu1—N31	2.0009 (15)	C14—C15	1.370 (3)
Cu1—N1	2.0855 (14)	C14—Cl14	1.743 (2)
Cu1—O4	2.2252 (13)	C15—C16	1.382 (3)
N1—C2	1.480 (2)	C15—H15	0.9300
N1—C6	1.489 (2)	C16—H16	0.9300
N1—C10	1.505 (2)	N21—C22	1.318 (2)
C2—C3	1.529 (3)	N21—C25	1.373 (2)
C2—H2A	0.9700	C22—N23	1.335 (2)
C2—H2B	0.9700	C22—H22	0.9300
C3—O5	1.229 (2)	N23—C24	1.357 (3)
C3—O4	1.268 (2)	N23—H23	0.8528
C6—C7	1.522 (2)	C24—C25	1.343 (3)
C6—H6A	0.9700	C24—H24	0.9300
C6—H6B	0.9700	C25—H25	0.9300
C7—O9	1.237 (2)	N31—C32	1.322 (2)
C7—O8	1.274 (2)	N31—C35	1.383 (2)
C10—C11	1.500 (3)	C32—N33	1.329 (3)
C10—H10A	0.9700	C32—H32	0.9300
C10—H10B	0.9700	N33—C34	1.366 (3)
C11—C12	1.383 (3)	N33—H33	0.8605
C11—C16	1.386 (3)	C34—C35	1.353 (3)
C12—C13	1.389 (3)	C34—H34	0.9300
C12—H12	0.9300	C35—H35	0.9300

O8—Cu1—N21	89.70 (6)	C11—C12—C13	120.84 (19)
O8—Cu1—N31	152.89 (6)	C11—C12—H12	119.6
N21—Cu1—N31	92.12 (6)	C13—C12—H12	119.6
O8—Cu1—N1	84.05 (5)	C14—C13—C12	118.28 (19)
N21—Cu1—N1	169.05 (6)	C14—C13—H13	120.9
N31—Cu1—N1	97.54 (6)	C12—C13—H13	120.9
O8—Cu1—O4	108.66 (6)	C15—C14—C13	122.3 (2)
N21—Cu1—O4	96.01 (6)	C15—C14—Cl14	118.91 (18)
N31—Cu1—O4	98.04 (6)	C13—C14—Cl14	118.83 (18)
N1—Cu1—O4	77.60 (5)	C14—C15—C16	118.7 (2)
C2—N1—C6	109.27 (14)	C14—C15—H15	120.7
C2—N1—C10	108.01 (14)	C16—C15—H15	120.7
C6—N1—C10	111.90 (14)	C15—C16—C11	120.8 (2)
C2—N1—Cu1	108.30 (11)	C15—C16—H16	119.6
C6—N1—Cu1	103.12 (10)	C11—C16—H16	119.6
C10—N1—Cu1	116.03 (11)	C22—N21—C25	105.20 (16)
N1—C2—C3	112.27 (15)	C22—N21—Cu1	124.73 (13)
N1—C2—H2A	109.2	C25—N21—Cu1	128.92 (14)
C3—C2—H2A	109.2	N21—C22—N23	111.10 (17)
N1—C2—H2B	109.2	N21—C22—H22	124.4
C3—C2—H2B	109.2	N23—C22—H22	124.4
H2A—C2—H2B	107.9	C22—N23—C24	107.64 (17)
O5—C3—O4	126.93 (19)	C22—N23—H23	129.6
O5—C3—C2	117.70 (17)	C24—N23—H23	121.6
O4—C3—C2	115.28 (16)	C25—C24—N23	106.28 (19)
C3—O4—Cu1	114.37 (12)	C25—C24—H24	126.9
N1—C6—C7	111.90 (14)	N23—C24—H24	126.9
N1—C6—H6A	109.2	C24—C25—N21	109.77 (19)
C7—C6—H6A	109.2	C24—C25—H25	125.1
N1—C6—H6B	109.2	N21—C25—H25	125.1
C7—C6—H6B	109.2	C32—N31—C35	105.33 (16)
H6A—C6—H6B	107.9	C32—N31—Cu1	125.97 (13)
O9—C7—O8	124.87 (17)	C35—N31—Cu1	126.20 (13)
O9—C7—C6	119.27 (15)	N31—C32—N33	111.45 (18)
O8—C7—C6	115.78 (15)	N31—C32—H32	124.3
C7—O8—Cu1	116.00 (11)	N33—C32—H32	124.3
C11—C10—N1	113.20 (15)	C32—N33—C34	107.75 (17)
C11—C10—H10A	108.9	C32—N33—H33	121.7
N1—C10—H10A	108.9	C34—N33—H33	129.8
C11—C10—H10B	108.9	C35—C34—N33	106.30 (18)
N1—C10—H10B	108.9	C35—C34—H34	126.9
H10A—C10—H10B	107.8	N33—C34—H34	126.9
C12—C11—C16	119.00 (19)	C34—C35—N31	109.17 (18)
C12—C11—C10	121.28 (18)	C34—C35—H35	125.4
C16—C11—C10	119.72 (19)	N31—C35—H35	125.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N23—H23···O4ⁱ	0.85	1.90	2.733 (2)	164
N33—H33···O9ⁱⁱ	0.86	1.93	2.779 (2)	169

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₁₀ClNO₄)(C₃H₄N)₂]
M_r	455.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.2028 (5), 13.4280 (6), 13.9113 (7)
β (°)	97.119 (1)
V (Å³)	1891.20 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.49 × 0.32 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.562, 0.825
No. of measured, independent and observed [I > 2σ(I)] reflections	21629, 4437, 4043
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 1.05
No. of reflections	4437
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.48

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL, PLATON (Spek, 2003), publCIF (Westrip, 2007).

Selected geometric parameters (Å, º) top

Cu1—O8	1.9556 (13)	Cu1—N1	2.0855 (14)
Cu1—N21	1.9874 (15)	Cu1—O4	2.2252 (13)
Cu1—N31	2.0009 (15)

O8—Cu1—N21	89.70 (6)	N31—Cu1—N1	97.54 (6)
O8—Cu1—N31	152.89 (6)	O8—Cu1—O4	108.66 (6)
N21—Cu1—N31	92.12 (6)	N21—Cu1—O4	96.01 (6)
O8—Cu1—N1	84.05 (5)	N31—Cu1—O4	98.04 (6)
N21—Cu1—N1	169.05 (6)	N1—Cu1—O4	77.60 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N23—H23···O4ⁱ	0.85	1.90	2.733 (2)	163.5
N33—H33···O9ⁱⁱ	0.86	1.93	2.779 (2)	168.5

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

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