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The unexpected title compound, [Cu(C6H8NO6)Cl(H2O)]·C12H24O6·3H2O, was synthesized by crystallization of a mixture containing CuCl2·2H2O, nitrilo­triacetic acid (H3NTA), KOH, 18-crown-6 and GdCl3·6H2O. The complex consists of a hydrogen-bonded polymeric structure, in which discrete Cu(H2NTA)(H2O)Cl units inter­act via the carboxyl groups and the coordinating water mol­ecules with the crown ether molecules. No direct metal–crown ether bond exists in the infinite sandwich-type hydrogen-bonded structure. The copper complex lies on a mirror plane, which passes through Cu and all the coordinating atoms. The crown ether molecule lies on an inversion centre. One water molecule is disordered across the mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008427/ww6365sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008427/ww6365Isup2.hkl
Contains datablock I

CCDC reference: 605212

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 96%
  • Disorder in solvent or counterion
  • R factor = 0.037
  • wR factor = 0.076
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O10 .. 2.77 Ang. PLAT430_ALERT_2_B Short Inter D...A Contact O2 .. O10 .. 2.77 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 16 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc. PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O10 .. 2.85 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O1 .. O10 .. 2.85 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 O
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C18 H40 Cl1 Cu1 N1 O16 Atom count from the _atom_site data: C18 H38 Cl1 Cu1 N1 O16 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C18 H40 Cl Cu N O16 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 72.00 72.00 0.00 H 160.00 152.00 8.00 Cl 4.00 4.00 0.00 Cu 4.00 4.00 0.00 N 4.00 4.00 0.00 O 64.00 64.00 0.00
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 4 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

aquachloro(nitrilotriacetato-κ2N,O)copper(II) 18-crown-6-ether trihydrate top
Crystal data top
[Cu(C6H8NO6)Cl(H2O)]·C12H24O6·3H2ODx = 1.447 Mg m3
Mr = 625.50Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 1435 reflections
a = 7.542 (2) Åθ = 2.4–25.0°
b = 24.569 (5) ŵ = 0.92 mm1
c = 15.493 (3) ÅT = 293 K
V = 2870.8 (10) Å3Plate, light blue
Z = 40.30 × 0.11 × 0.05 mm
F(000) = 1316
Data collection top
Bruker SMART CCD area-detector
diffractometer
2559 independent reflections
Radiation source: fine-focus sealed tube2189 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 88
Tmin = 0.763, Tmax = 0.955k = 2925
13134 measured reflectionsl = 1817
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.076H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.01P)2 + 3P]
where P = (Fo2 + 2Fc2)/3
2559 reflections(Δ/σ)max = 0.001
236 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.40 e Å3
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 > 2σ(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
xyzUiso*/UeqOcc. (<1)
Cu10.21170 (6)0.75000.98169 (3)0.03632 (14)
O20.6780 (3)0.75001.09827 (16)0.0444 (6)
O30.0342 (4)0.75001.07259 (16)0.0741 (10)
N10.4262 (4)0.75000.89794 (17)0.0364 (7)
Cl10.01211 (13)0.75000.87478 (6)0.0571 (3)
O80.7243 (3)0.89947 (9)1.01043 (15)0.0659 (6)
O90.3258 (3)0.98168 (8)0.92845 (13)0.0653 (6)
O60.2058 (3)1.01134 (10)1.10057 (14)0.0678 (6)
O70.4774 (3)0.93137 (8)1.14184 (13)0.0609 (6)
O10.3886 (3)0.75001.07415 (14)0.0371 (6)
C20.5483 (5)0.75001.0494 (2)0.0346 (8)
C30.4234 (4)0.70101 (11)0.84296 (17)0.0430 (6)
H3B0.534 (4)0.6940 (10)0.8155 (17)0.052*
H3A0.339 (4)0.7042 (11)0.8013 (18)0.052*
C10.5864 (6)0.75000.9539 (3)0.0484 (11)
H1A0.653 (11)0.790 (2)0.947 (5)0.058*0.50
H1B0.667 (10)0.729 (3)0.936 (4)0.058*0.50
C90.7378 (6)0.88562 (14)1.0983 (3)0.0716 (11)
H9A0.806 (5)0.9159 (14)1.129 (2)0.086*
H9B0.801 (5)0.8530 (15)1.104 (2)0.086*
C70.2951 (6)0.92705 (19)1.1601 (3)0.0810 (12)
H7A0.284 (5)0.9068 (15)1.208 (2)0.097*
H7B0.226 (5)0.9101 (15)1.110 (3)0.097*
C50.1351 (6)1.06437 (19)1.1126 (3)0.0830 (12)
H5A0.221 (5)1.0854 (15)1.149 (3)0.100*
H5B0.024 (6)1.0589 (15)1.141 (2)0.100*
C60.2212 (6)0.9812 (2)1.1784 (2)0.0879 (13)
H6A0.110 (6)0.9768 (16)1.200 (3)0.105*
H6B0.297 (5)1.0047 (15)1.216 (3)0.105*
C80.5581 (6)0.87943 (13)1.1340 (2)0.0689 (10)
H8A0.490 (5)0.8563 (14)1.098 (2)0.083*
H8B0.560 (5)0.8626 (13)1.191 (2)0.083*
C100.8915 (6)0.90995 (19)0.9725 (3)0.0859 (13)
H10A0.949 (6)0.8771 (16)0.968 (2)0.103*
H10B0.962 (6)0.9334 (16)1.006 (2)0.103*
O40.2962 (3)0.65384 (7)0.96233 (11)0.0476 (5)
O50.4084 (3)0.60670 (9)0.85228 (14)0.0644 (6)
C40.3702 (4)0.65139 (10)0.89324 (16)0.0424 (6)
H5C0.380 (5)0.5810 (13)0.878 (2)0.064 (11)*
O100.1830 (6)0.73098 (17)1.2257 (2)0.0709 (17)0.50
H9C0.39301.00850.91390.050*
H9D0.30860.99070.98140.050*
H3D0.05900.75001.12680.050*
H3C0.07980.75001.06820.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0263 (2)0.0541 (3)0.0286 (2)0.0000.00032 (18)0.000
O20.0265 (15)0.0620 (17)0.0446 (14)0.0000.0057 (11)0.000
O30.0282 (16)0.163 (3)0.0312 (14)0.0000.0022 (12)0.000
N10.0358 (18)0.0446 (17)0.0288 (14)0.0000.0017 (13)0.000
Cl10.0369 (6)0.0976 (8)0.0367 (5)0.0000.0069 (4)0.000
O80.0549 (14)0.0700 (14)0.0728 (15)0.0086 (11)0.0112 (12)0.0094 (11)
O90.0795 (17)0.0475 (12)0.0689 (14)0.0101 (10)0.0152 (12)0.0055 (10)
O60.0587 (15)0.0862 (16)0.0584 (13)0.0039 (12)0.0106 (11)0.0099 (12)
O70.0696 (16)0.0558 (13)0.0573 (12)0.0139 (11)0.0018 (11)0.0014 (10)
O10.0275 (14)0.0524 (15)0.0314 (12)0.0000.0001 (10)0.000
C20.028 (2)0.0367 (19)0.0393 (18)0.0000.0014 (16)0.000
C30.0465 (18)0.0475 (16)0.0348 (14)0.0023 (13)0.0086 (13)0.0033 (11)
C10.024 (2)0.078 (3)0.043 (2)0.0000.0053 (17)0.000
C90.076 (3)0.0490 (19)0.090 (3)0.0040 (18)0.035 (2)0.0020 (18)
C70.084 (3)0.096 (3)0.062 (2)0.024 (2)0.011 (2)0.021 (2)
C50.054 (2)0.104 (3)0.091 (3)0.003 (2)0.020 (2)0.027 (2)
C60.075 (3)0.131 (4)0.057 (2)0.008 (3)0.023 (2)0.003 (2)
C80.092 (3)0.0486 (19)0.067 (2)0.0151 (18)0.028 (2)0.0062 (16)
C100.053 (3)0.086 (3)0.119 (4)0.021 (2)0.004 (2)0.017 (3)
O40.0509 (12)0.0493 (11)0.0427 (10)0.0016 (9)0.0069 (9)0.0034 (8)
O50.0946 (19)0.0436 (12)0.0549 (13)0.0044 (12)0.0166 (12)0.0033 (10)
C40.0422 (16)0.0452 (15)0.0399 (14)0.0029 (12)0.0014 (12)0.0023 (12)
O100.061 (3)0.112 (5)0.0391 (19)0.012 (2)0.0032 (18)0.0116 (19)
Geometric parameters (Å, º) top
Cu1—O31.943 (3)C1—H1A1.10 (8)
Cu1—O11.958 (2)C1—H1B0.85 (8)
Cu1—N12.074 (3)C9—C81.472 (6)
Cu1—Cl12.238 (1)C9—H9A1.02 (4)
O2—C21.236 (4)C9—H9B0.94 (4)
O3—H3D0.8602C7—C61.470 (6)
O3—H3C0.8629C7—H7A0.90 (4)
N1—C31.475 (3)C7—H7B1.02 (4)
N1—C3i1.475 (3)C5—C10ii1.475 (6)
N1—C11.488 (5)C5—H5A1.00 (4)
O8—C91.407 (4)C5—H5B0.96 (4)
O8—C101.415 (5)C6—H6A0.91 (4)
O9—H9C0.8613C6—H6B1.00 (4)
O9—H9D0.8604C8—H8A0.95 (4)
O6—C61.419 (5)C8—H8B0.98 (3)
O6—C51.420 (5)C10—C5ii1.475 (6)
O7—C71.407 (5)C10—H10A0.92 (4)
O7—C81.419 (4)C10—H10B0.94 (4)
O1—C21.264 (4)O4—C41.208 (3)
C2—C11.507 (5)O5—C41.300 (3)
C3—C41.501 (4)O5—H5C0.78 (3)
C3—H3B0.95 (3)O10—O10i0.934 (8)
C3—H3A0.91 (3)
O3—Cu1—O186.5 (1)O8—C9—H9B110 (2)
O3—Cu1—N1172.3 (1)C8—C9—H9B110 (2)
O1—Cu1—N185.8 (1)H9A—C9—H9B109 (3)
O3—Cu1—Cl194.19 (9)O7—C7—C6109.9 (3)
O1—Cu1—Cl1179.30 (8)O7—C7—H7A107 (3)
N1—Cu1—Cl193.53 (8)C6—C7—H7A108 (2)
Cu1—O3—H3D123.9O7—C7—H7B112 (2)
Cu1—O3—H3C129.0C6—C7—H7B109 (2)
H3D—O3—H3C107.0H7A—C7—H7B111 (3)
C3—N1—C3i109.4 (3)O6—C5—C10ii109.1 (3)
C3—N1—C1110.4 (2)O6—C5—H5A108 (2)
C3i—N1—C1110.4 (2)C10ii—C5—H5A112 (2)
C3—N1—Cu1110.49 (17)O6—C5—H5B105 (2)
C3i—N1—Cu1110.49 (17)C10ii—C5—H5B111 (2)
C1—N1—Cu1105.6 (2)H5A—C5—H5B112 (3)
C9—O8—C10112.4 (3)O6—C6—C7109.9 (3)
H9C—O9—H9D98.0O6—C6—H6A107 (3)
C6—O6—C5113.5 (3)C7—C6—H6A108 (3)
C7—O7—C8111.6 (3)O6—C6—H6B104 (2)
C2—O1—Cu1115.3 (2)C7—C6—H6B115 (2)
O2—C2—O1124.6 (3)H6A—C6—H6B113 (3)
O2—C2—C1116.7 (3)O7—C8—C9109.5 (3)
O1—C2—C1118.6 (3)O7—C8—H8A111 (2)
N1—C3—C4111.5 (2)C9—C8—H8A110 (2)
N1—C3—H3B113.1 (17)O7—C8—H8B108 (2)
C4—C3—H3B108.7 (16)C9—C8—H8B112 (2)
N1—C3—H3A110.5 (17)H8A—C8—H8B107 (3)
C4—C3—H3A104.6 (18)O8—C10—C5ii109.2 (3)
H3B—C3—H3A108 (2)O8—C10—H10A107 (3)
N1—C1—C2114.7 (3)C5ii—C10—H10A112 (2)
N1—C1—H1A108 (4)O8—C10—H10B113 (3)
C2—C1—H1A101 (4)C5ii—C10—H10B108 (3)
N1—C1—H1B113 (5)H10A—C10—H10B108 (4)
C2—C1—H1B117 (5)C4—O5—H5C112 (2)
H1A—C1—H1B101 (5)O4—C4—O5125.2 (3)
O8—C9—C8108.8 (3)O4—C4—C3122.9 (2)
O8—C9—H9A108.1 (19)O5—C4—C3111.9 (2)
C8—C9—H9A111 (2)
Symmetry codes: (i) x, y+3/2, z; (ii) x+1, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5C···O9i0.78 (3)1.77 (3)2.549 (3)173.8 (3)
O9—H9C···O7ii0.861.972.820 (3)169
O9—H9D···O60.862.072.909 (3)167
O3—H3D···O10i0.861.862.666 (3)156
O3—H3D···O100.861.862.666 (3)156
O3—H3C···O2iii0.861.892.716 (3)161
Symmetry codes: (i) x, y+3/2, z; (ii) x+1, y+2, z+2; (iii) x1, y, z.
 

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