(N-Salicyl­idene-d,l-glutamato)(2-methyl­imidazole)copper(II)

Langer, V.; Scholtzová, E.; Gyepesová, D.; Kohútová, M.; Valent, A.

doi:10.1107/S1600536803028769

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(N-Salicylidene-D,L-glutamato)(2-methylimidazole)copper(II)

V. Langer, E. Scholtzová, D. Gyepesová, M. Kohútová and A. Valent

The title racemic compound, [Cu(C₁₂H₁₁NO₅)(C₄H₆N₂)], adopts a square-pyramidal Cu^II coordination with the tridentate N-salicylideneglutamate Schiff base dianion and the 2-methylimidazole ligand in the basal plane. The apex of the pyramid is occupied by a carboxylic acid O atom from the neighbouring chelate at a distance of 2.479 (4) Å, leading to infinite one-dimensional chains along the crystallographic a axis. Strong N—H

O and O—H

O hydrogen bonds form a helix parallel to the c axis. The electronic structure of the title compound has also been investigated by the B3LYP method.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028769/cf6312sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028769/cf6312Isup2.hkl Contains datablock I

CCDC reference: 231841

checkCIF report

Key indicators

Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.009 Å
R factor = 0.046
wR factor = 0.108
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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           25.04
           From the CIF: _reflns_number_total               2849
           Count of symmetry unique reflns         1448
           Completeness (_total/calc)            196.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1401
           Fraction of Friedel pairs measured     0.968
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 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: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.

(N-Salicylidene-DL-glutamato)(2-methylimidazole)copper(II) top

Crystal data top

[Cu(C₁₂H₁₁NO₅)(C₄H₆N₂)]	F(000) = 406
M_r = 394.87	D_x = 1.616 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 5004 reflections
a = 5.2319 (1) Å	θ = 2.5–25.0°
b = 16.2576 (3) Å	µ = 1.38 mm⁻¹
c = 9.6044 (1) Å	T = 183 K
β = 96.530 (1)°	Needle, blue
V = 811.63 (2) Å³	0.15 × 0.02 × 0.02 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	2849 independent reflections
Radiation source: fine-focus sealed tube	2512 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −6→6
T_min = 0.820, T_max = 0.980	k = −19→19
7539 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0623P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2849 reflections	Δρ_max = 0.41 e Å⁻³
229 parameters	Δρ_min = −0.42 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1181 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (2)

Special details top

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 60 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 5004 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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	0.36104 (8)	0.20165 (3)	0.75965 (7)	0.01363 (17)
O1	0.5828 (8)	0.2631 (2)	0.6472 (4)	0.0171 (8)
O2	0.0957 (7)	0.1468 (2)	0.8587 (4)	0.0151 (8)
O3	−0.2754 (7)	0.1748 (2)	0.9430 (4)	0.0201 (9)
O4	0.2575 (9)	0.3256 (3)	1.3647 (4)	0.0363 (12)
O5	0.5298 (8)	0.2184 (2)	1.3767 (4)	0.0266 (10)
H5	0.5760	0.2371	1.4572	0.032*
N1	0.2319 (9)	0.3007 (3)	0.8415 (5)	0.0144 (10)
N2	0.4145 (8)	0.0965 (3)	0.6633 (5)	0.0184 (10)
N3	0.3345 (11)	−0.0142 (3)	0.5366 (5)	0.0298 (13)
H3	0.2625	−0.0477	0.4715	0.036*
C1	0.2842 (13)	0.3752 (4)	0.8116 (7)	0.0209 (16)
H1	0.1888	0.4175	0.8503	0.025*
C2	0.4789 (13)	0.4001 (4)	0.7227 (7)	0.0190 (14)
C3	0.5174 (13)	0.4855 (4)	0.7117 (7)	0.0317 (15)
H3A	0.4216	0.5222	0.7625	0.038*
C4	0.6907 (14)	0.5162 (4)	0.6287 (8)	0.0373 (17)
H4	0.7164	0.5738	0.6213	0.045*
C5	0.8288 (13)	0.4609 (4)	0.5552 (7)	0.0368 (17)
H5A	0.9504	0.4815	0.4977	0.044*
C6	0.7933 (11)	0.3765 (4)	0.5639 (6)	0.0269 (14)
H6	0.8922	0.3405	0.5135	0.032*
C7	0.6143 (11)	0.3442 (4)	0.6458 (6)	0.0209 (13)
C8	0.0189 (11)	0.2856 (3)	0.9271 (6)	0.0171 (12)
H8	−0.1290	0.3219	0.8923	0.020*
C9	0.0956 (10)	0.3036 (3)	1.0849 (5)	0.0166 (11)
H9A	0.1582	0.3610	1.0949	0.020*
H9B	−0.0599	0.2993	1.1343	0.020*
C10	0.3008 (12)	0.2470 (4)	1.1558 (6)	0.0201 (14)
H10A	0.2410	0.1893	1.1464	0.024*
H10B	0.4596	0.2521	1.1094	0.024*
C11	0.3589 (11)	0.2685 (4)	1.3095 (6)	0.0193 (13)
C12	−0.0663 (10)	0.1957 (3)	0.9081 (5)	0.0154 (11)
C13	0.5907 (12)	0.0364 (3)	0.7099 (7)	0.0252 (14)
H13	0.7246	0.0422	0.7848	0.030*
C14	0.5410 (12)	−0.0321 (4)	0.6311 (7)	0.0306 (15)
H14	0.6322	−0.0827	0.6401	0.037*
C15	0.2585 (11)	0.0637 (3)	0.5596 (6)	0.0232 (13)
C16	0.0393 (13)	0.1046 (4)	0.4758 (7)	0.0358 (16)
H16A	0.0341	0.1627	0.5025	0.043*
H16B	−0.1216	0.0778	0.4935	0.043*
H16C	0.0604	0.1003	0.3760	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0159 (3)	0.0111 (3)	0.0144 (3)	−0.0002 (4)	0.0040 (2)	−0.0013 (4)
O1	0.021 (2)	0.012 (2)	0.018 (2)	−0.0041 (17)	0.0000 (17)	0.0017 (17)
O2	0.013 (2)	0.014 (2)	0.020 (2)	0.0031 (15)	0.0060 (16)	0.0007 (15)
O3	0.019 (2)	0.023 (2)	0.019 (2)	−0.0043 (16)	0.0055 (17)	0.0004 (16)
O4	0.036 (3)	0.048 (3)	0.023 (2)	0.021 (2)	−0.002 (2)	−0.013 (2)
O5	0.033 (3)	0.031 (3)	0.014 (2)	0.010 (2)	−0.0040 (19)	−0.0033 (18)
N1	0.020 (3)	0.012 (2)	0.011 (2)	−0.002 (2)	−0.0003 (19)	0.004 (2)
N2	0.020 (3)	0.014 (2)	0.022 (2)	0.002 (2)	0.005 (2)	−0.003 (2)
N3	0.037 (3)	0.024 (3)	0.029 (4)	−0.012 (3)	0.009 (3)	−0.015 (2)
C1	0.029 (4)	0.013 (3)	0.020 (3)	0.001 (3)	0.002 (3)	−0.002 (3)
C2	0.022 (3)	0.014 (3)	0.020 (3)	−0.002 (3)	0.000 (3)	0.003 (3)
C3	0.033 (4)	0.020 (3)	0.041 (4)	−0.004 (3)	0.001 (3)	0.008 (3)
C4	0.046 (4)	0.016 (3)	0.050 (4)	−0.014 (3)	0.004 (4)	0.009 (3)
C5	0.031 (4)	0.039 (4)	0.041 (4)	−0.017 (3)	0.005 (3)	0.017 (3)
C6	0.024 (3)	0.030 (4)	0.027 (3)	−0.007 (3)	0.001 (3)	0.001 (3)
C7	0.023 (3)	0.025 (4)	0.013 (3)	−0.006 (3)	−0.001 (2)	0.006 (2)
C8	0.018 (3)	0.012 (3)	0.021 (3)	0.003 (2)	0.006 (2)	−0.001 (2)
C9	0.019 (3)	0.017 (3)	0.013 (3)	0.001 (2)	0.000 (2)	−0.002 (2)
C10	0.022 (4)	0.023 (3)	0.015 (3)	0.007 (3)	0.004 (3)	0.003 (3)
C11	0.018 (3)	0.021 (3)	0.019 (3)	−0.003 (2)	0.005 (3)	0.000 (2)
C12	0.018 (3)	0.019 (3)	0.008 (2)	−0.001 (2)	−0.001 (2)	0.000 (2)
C13	0.028 (3)	0.016 (3)	0.032 (3)	0.000 (2)	0.005 (3)	−0.004 (3)
C14	0.032 (4)	0.015 (3)	0.047 (4)	0.003 (3)	0.015 (3)	−0.009 (3)
C15	0.030 (3)	0.019 (3)	0.022 (3)	−0.008 (2)	0.007 (3)	−0.003 (2)
C16	0.040 (4)	0.030 (4)	0.034 (4)	−0.012 (3)	−0.009 (3)	0.000 (3)

Geometric parameters (Å, º) top

Cu1—N1	1.946 (5)	C3—H3A	0.950
Cu1—O1	1.948 (4)	C4—C5	1.394 (10)
Cu1—N2	1.979 (5)	C4—H4	0.950
Cu1—O2	1.982 (4)	C5—C6	1.387 (9)
Cu1—O3ⁱ	2.479 (4)	C5—H5A	0.950
O1—C7	1.328 (7)	C6—C7	1.393 (8)
O2—C12	1.291 (6)	C6—H6	0.950
O3—C12	1.228 (6)	C8—C12	1.532 (7)
O4—C11	1.221 (7)	C8—C9	1.551 (7)
O5—C11	1.322 (7)	C8—H8	1.000
O5—H5	0.840	C9—C10	1.516 (8)
N1—C1	1.282 (8)	C9—H9A	0.990
N1—C8	1.478 (7)	C9—H9B	0.990
N2—C15	1.325 (7)	C10—C11	1.513 (9)
N2—C13	1.382 (7)	C10—H10A	0.990
N3—C15	1.354 (8)	C10—H10B	0.990
N3—C14	1.361 (8)	C13—C14	1.355 (8)
N3—H3	0.880	C13—H13	0.950
C1—C2	1.459 (8)	C14—H14	0.950
C1—H1	0.950	C15—C16	1.482 (9)
C2—C3	1.409 (8)	C16—H16A	0.980
C2—C7	1.411 (9)	C16—H16B	0.980
C3—C4	1.368 (10)	C16—H16C	0.980

N1—Cu1—O1	93.2 (2)	N1—C8—C12	108.6 (4)
N1—Cu1—N2	167.84 (19)	N1—C8—C9	112.6 (4)
O1—Cu1—N2	93.41 (18)	C12—C8—C9	109.6 (4)
N1—Cu1—O2	83.31 (17)	N1—C8—H8	108.6
O1—Cu1—O2	172.15 (17)	C12—C8—H8	108.6
N2—Cu1—O2	88.86 (17)	C9—C8—H8	108.6
C7—O1—Cu1	126.7 (4)	C10—C9—C8	114.6 (5)
C12—O2—Cu1	115.1 (3)	C10—C9—H9A	108.6
C11—O5—H5	109.5	C8—C9—H9A	108.6
C1—N1—C8	118.3 (5)	C10—C9—H9B	108.6
C1—N1—Cu1	126.8 (5)	C8—C9—H9B	108.6
C8—N1—Cu1	114.0 (3)	H9A—C9—H9B	107.6
C15—N2—C13	106.9 (5)	C11—C10—C9	110.6 (5)
C15—N2—Cu1	126.2 (4)	C11—C10—H10A	109.5
C13—N2—Cu1	125.7 (4)	C9—C10—H10A	109.5
C15—N3—C14	108.5 (5)	C11—C10—H10B	109.5
C15—N3—H3	125.8	C9—C10—H10B	109.5
C14—N3—H3	125.8	H10A—C10—H10B	108.1
N1—C1—C2	125.1 (6)	O4—C11—O5	124.0 (5)
N1—C1—H1	117.5	O4—C11—C10	123.4 (5)
C2—C1—H1	117.5	O5—C11—C10	112.6 (5)
C3—C2—C7	120.7 (6)	O3—C12—O2	124.9 (5)
C3—C2—C1	115.6 (6)	O3—C12—C8	119.2 (5)
C7—C2—C1	123.6 (5)	O2—C12—C8	115.9 (5)
C4—C3—C2	120.9 (7)	C14—C13—N2	108.8 (6)
C4—C3—H3A	119.6	C14—C13—H13	125.6
C2—C3—H3A	119.6	N2—C13—H13	125.6
C3—C4—C5	118.4 (6)	N3—C14—C13	106.5 (5)
C3—C4—H4	120.8	N3—C14—H14	126.8
C5—C4—H4	120.8	C13—C14—H14	126.8
C6—C5—C4	121.7 (6)	N2—C15—N3	109.4 (5)
C6—C5—H5A	119.1	N2—C15—C16	126.9 (5)
C4—C5—H5A	119.1	N3—C15—C16	123.7 (5)
C5—C6—C7	120.7 (6)	C15—C16—H16A	109.5
C5—C6—H6	119.7	C15—C16—H16B	109.5
C7—C6—H6	119.7	H16A—C16—H16B	109.5
O1—C7—C2	124.3 (5)	C15—C16—H16C	109.5
O1—C7—C6	118.2 (5)	H16A—C16—H16C	109.5
C2—C7—C6	117.5 (6)	H16B—C16—H16C	109.5

N1—Cu1—O1—C7	2.0 (4)	C3—C2—C7—C6	2.6 (9)
N2—Cu1—O1—C7	171.8 (4)	C1—C2—C7—C6	179.4 (5)
N1—Cu1—O2—C12	11.6 (4)	C5—C6—C7—O1	178.1 (5)
N2—Cu1—O2—C12	−159.1 (4)	C5—C6—C7—C2	−2.3 (9)
O1—Cu1—N1—C1	3.8 (5)	C1—N1—C8—C12	161.2 (5)
N2—Cu1—N1—C1	−118.9 (10)	Cu1—N1—C8—C12	−8.4 (5)
O2—Cu1—N1—C1	−169.1 (5)	C1—N1—C8—C9	−77.2 (6)
O1—Cu1—N1—C8	172.4 (3)	Cu1—N1—C8—C9	113.2 (4)
N2—Cu1—N1—C8	49.7 (11)	N1—C8—C9—C10	−65.4 (6)
O2—Cu1—N1—C8	−0.5 (3)	C12—C8—C9—C10	55.6 (6)
N1—Cu1—N2—C15	24.9 (12)	C8—C9—C10—C11	−179.0 (5)
O1—Cu1—N2—C15	−97.8 (5)	C9—C10—C11—O4	−2.2 (8)
O2—Cu1—N2—C15	74.7 (5)	C9—C10—C11—O5	177.5 (5)
N1—Cu1—N2—C13	−140.9 (8)	Cu1—O2—C12—O3	162.2 (4)
O1—Cu1—N2—C13	96.4 (5)	Cu1—O2—C12—C8	−19.6 (6)
O2—Cu1—N2—C13	−91.2 (5)	N1—C8—C12—O3	−163.4 (5)
C8—N1—C1—C2	−176.7 (5)	C9—C8—C12—O3	73.1 (6)
Cu1—N1—C1—C2	−8.6 (8)	N1—C8—C12—O2	18.3 (6)
N1—C1—C2—C3	−175.7 (6)	C9—C8—C12—O2	−105.1 (5)
N1—C1—C2—C7	7.4 (9)	C15—N2—C13—C14	1.1 (7)
C7—C2—C3—C4	−1.5 (10)	Cu1—N2—C13—C14	169.2 (4)
C1—C2—C3—C4	−178.5 (6)	C15—N3—C14—C13	−0.9 (7)
C2—C3—C4—C5	0.0 (10)	N2—C13—C14—N3	−0.1 (7)
C3—C4—C5—C6	0.4 (10)	C13—N2—C15—N3	−1.7 (7)
C4—C5—C6—C7	0.8 (10)	Cu1—N2—C15—N3	−169.7 (4)
Cu1—O1—C7—C2	−3.2 (8)	C13—N2—C15—C16	−179.6 (6)
Cu1—O1—C7—C6	176.4 (4)	Cu1—N2—C15—C16	12.4 (9)
C3—C2—C7—O1	−177.8 (5)	C14—N3—C15—N2	1.6 (7)
C1—C2—C7—O1	−1.1 (9)	C14—N3—C15—C16	179.6 (6)

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2ⁱⁱ	0.88	2.08	2.940 (6)	166
O5—H5···O1ⁱⁱⁱ	0.84	1.87	2.682 (6)	162
C6—H6···O4^iv	0.95	2.52	3.362 (8)	147
C10—H10B···O3ⁱ	0.99	2.56	3.391 (7)	142
C14—H14···O3^v	0.95	2.50	3.157 (7)	126

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

Bond distances d(Cu—X) (Å) and Mulliken population analysis (|e|) for Cu and neighbouring atoms (X) top

Atom X	d(Cu—X)	Mulliken charges	Overlap population
Cu1		0.821
N1	1.946 (5)	-0.323	0.164
N2	1.947 (4)	-0.333	0.178
O1	1.950 (4)	-0.378	0.204
O2	1.984 (4)	-0.394	0.205

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