In the title compound, [Cu(C
11H
14N
3O
4)(H
2O)]ClO
4, the Cu
II ion is five-coordinated in a square-pyramidal configuration, with one imine N, one amine N, one phenolate O, and one hydroxyl O atom of the Schiff base defining the basal plane, and the O atom of a coordinated water molecule occupying the apical position. In the crystal structure, the molecules are linked through intermolecular O—H
O and N—H
O hydrogen bonds, forming chains running along the
b axis.
Supporting information
CCDC reference: 610736
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- Disorder in solvent or counterion
- R factor = 0.078
- wR factor = 0.202
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X H4A .. H10B .. 2.08 Ang.
Alert level C
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 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
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Aqua[2-[2-(2-hydroxyethylamino)ethyliminomethyl]-4-nitro-phenolato]copper(II)
perchlorate
top
Crystal data top
[Cu(C11H14N3O4)(H2O)]ClO4 | F(000) = 1768 |
Mr = 433.26 | Dx = 1.766 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2237 reflections |
a = 19.552 (2) Å | θ = 2.1–25.0° |
b = 11.859 (1) Å | µ = 1.56 mm−1 |
c = 14.658 (2) Å | T = 298 K |
β = 106.488 (1)° | Block, blue |
V = 3259.0 (6) Å3 | 0.29 × 0.21 × 0.15 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3193 independent reflections |
Radiation source: fine-focus sealed tube | 2722 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→23 |
Tmin = 0.661, Tmax = 0.800 | k = −14→14 |
12264 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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.202 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0862P)2 + 19.9923P] where P = (Fo2 + 2Fc2)/3 |
3193 reflections | (Δ/σ)max = 0.001 |
263 parameters | Δρmax = 1.07 e Å−3 |
79 restraints | Δρmin = −0.67 e Å−3 |
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 | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.06078 (4) | 0.10513 (7) | 0.39151 (6) | 0.0466 (3) | |
Cl1 | 0.27368 (11) | 0.0705 (3) | 0.11243 (16) | 0.0827 (7) | |
O1 | −0.0515 (3) | 0.6988 (5) | 0.3520 (6) | 0.092 (2) | |
O2 | −0.1423 (3) | 0.6617 (5) | 0.4012 (4) | 0.0759 (16) | |
O3 | −0.0243 (2) | 0.1766 (4) | 0.3970 (4) | 0.0575 (13) | |
O4 | 0.0200 (3) | −0.0497 (4) | 0.3784 (4) | 0.0620 (13) | |
H4A | −0.0278 | −0.0658 | 0.3709 | 0.093* | |
O5 | 0.1012 (3) | 0.0927 (4) | 0.5621 (3) | 0.0625 (13) | |
H5A | 0.1302 | 0.0394 | 0.5647 | 0.094* | |
H5B | 0.1237 | 0.1496 | 0.5885 | 0.094* | |
N1 | −0.0898 (3) | 0.6321 (5) | 0.3786 (4) | 0.0574 (15) | |
N2 | 0.1056 (3) | 0.2408 (5) | 0.3658 (4) | 0.0459 (13) | |
N3 | 0.1455 (3) | 0.0272 (5) | 0.3713 (4) | 0.0476 (13) | |
H3A | 0.1787 | 0.0188 | 0.4287 | 0.057* | |
C1 | 0.0108 (3) | 0.3669 (6) | 0.3740 (4) | 0.0423 (14) | |
C2 | −0.0367 (3) | 0.2833 (6) | 0.3921 (4) | 0.0447 (15) | |
C3 | −0.1017 (3) | 0.3236 (7) | 0.4040 (5) | 0.0554 (18) | |
H3 | −0.1340 | 0.2714 | 0.4151 | 0.067* | |
C4 | −0.1193 (4) | 0.4347 (7) | 0.4001 (5) | 0.0531 (17) | |
H4 | −0.1623 | 0.4577 | 0.4093 | 0.064* | |
C5 | −0.0718 (3) | 0.5140 (6) | 0.3821 (4) | 0.0456 (15) | |
C6 | −0.0079 (3) | 0.4792 (6) | 0.3690 (4) | 0.0466 (15) | |
H6 | 0.0232 | 0.5326 | 0.3566 | 0.056* | |
C7 | 0.0791 (3) | 0.3383 (6) | 0.3590 (4) | 0.0476 (16) | |
H7 | 0.1054 | 0.3966 | 0.3430 | 0.057* | |
C8 | 0.1761 (4) | 0.2197 (7) | 0.3513 (6) | 0.062 (2) | |
H8A | 0.2133 | 0.2262 | 0.4111 | 0.075* | |
H8B | 0.1855 | 0.2741 | 0.3068 | 0.075* | |
C9 | 0.1746 (4) | 0.1021 (7) | 0.3120 (5) | 0.0583 (19) | |
H9A | 0.1449 | 0.0998 | 0.2466 | 0.070* | |
H9B | 0.2224 | 0.0784 | 0.3136 | 0.070* | |
C10 | 0.1239 (4) | −0.0853 (7) | 0.3312 (6) | 0.065 (2) | |
H10A | 0.1654 | −0.1335 | 0.3402 | 0.078* | |
H10B | 0.1003 | −0.0797 | 0.2635 | 0.078* | |
C11 | 0.0739 (5) | −0.1336 (7) | 0.3819 (7) | 0.074 (2) | |
H11A | 0.0523 | −0.2024 | 0.3509 | 0.088* | |
H11B | 0.0994 | −0.1510 | 0.4474 | 0.088* | |
O6 | 0.2776 (5) | −0.0161 (9) | 0.0421 (6) | 0.076 (4) | 0.529 (13) |
O7 | 0.3029 (9) | 0.0185 (13) | 0.2007 (7) | 0.122 (5) | 0.529 (13) |
O8 | 0.2004 (5) | 0.0850 (11) | 0.0977 (10) | 0.102 (5) | 0.529 (13) |
O9 | 0.3092 (11) | 0.1643 (12) | 0.0984 (16) | 0.199 (8) | 0.529 (13) |
O6' | 0.2579 (12) | 0.076 (2) | 0.0155 (7) | 0.186 (8) | 0.471 (13) |
O7' | 0.3469 (5) | 0.0943 (12) | 0.1533 (12) | 0.108 (6) | 0.471 (13) |
O8' | 0.2416 (12) | 0.1682 (13) | 0.1427 (17) | 0.209 (13) | 0.471 (13) |
O9' | 0.2527 (12) | −0.0214 (13) | 0.1537 (16) | 0.171 (10) | 0.471 (13) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0414 (5) | 0.0538 (5) | 0.0491 (5) | −0.0059 (4) | 0.0202 (3) | 0.0022 (4) |
Cl1 | 0.0541 (11) | 0.122 (2) | 0.0702 (13) | 0.0251 (12) | 0.0148 (10) | 0.0013 (13) |
O1 | 0.072 (4) | 0.055 (3) | 0.152 (7) | −0.007 (3) | 0.033 (4) | 0.005 (4) |
O2 | 0.072 (4) | 0.074 (4) | 0.081 (4) | 0.014 (3) | 0.022 (3) | −0.015 (3) |
O3 | 0.044 (3) | 0.050 (3) | 0.087 (4) | −0.006 (2) | 0.031 (2) | 0.009 (2) |
O4 | 0.054 (3) | 0.058 (3) | 0.079 (3) | −0.021 (2) | 0.028 (3) | −0.014 (3) |
O5 | 0.076 (4) | 0.062 (3) | 0.053 (3) | 0.002 (3) | 0.025 (3) | −0.001 (2) |
N1 | 0.052 (3) | 0.056 (4) | 0.055 (4) | 0.003 (3) | −0.001 (3) | −0.010 (3) |
N2 | 0.033 (3) | 0.057 (4) | 0.049 (3) | −0.007 (2) | 0.014 (2) | 0.007 (3) |
N3 | 0.043 (3) | 0.058 (3) | 0.041 (3) | 0.000 (2) | 0.011 (2) | 0.004 (2) |
C1 | 0.034 (3) | 0.058 (4) | 0.034 (3) | −0.006 (3) | 0.007 (2) | 0.001 (3) |
C2 | 0.032 (3) | 0.057 (4) | 0.044 (3) | −0.008 (3) | 0.010 (2) | −0.002 (3) |
C3 | 0.039 (3) | 0.073 (5) | 0.057 (4) | −0.005 (3) | 0.018 (3) | 0.014 (4) |
C4 | 0.039 (3) | 0.075 (5) | 0.046 (4) | 0.009 (3) | 0.013 (3) | 0.005 (3) |
C5 | 0.039 (3) | 0.057 (4) | 0.034 (3) | 0.001 (3) | 0.001 (2) | −0.001 (3) |
C6 | 0.037 (3) | 0.059 (4) | 0.040 (3) | −0.010 (3) | 0.004 (2) | −0.005 (3) |
C7 | 0.039 (3) | 0.061 (4) | 0.044 (3) | −0.011 (3) | 0.013 (3) | 0.009 (3) |
C8 | 0.038 (4) | 0.079 (5) | 0.078 (5) | −0.002 (3) | 0.030 (3) | 0.017 (4) |
C9 | 0.047 (4) | 0.079 (5) | 0.056 (4) | 0.009 (4) | 0.026 (3) | 0.015 (4) |
C10 | 0.057 (4) | 0.066 (5) | 0.077 (5) | 0.001 (4) | 0.025 (4) | −0.012 (4) |
C11 | 0.079 (6) | 0.048 (4) | 0.097 (7) | −0.006 (4) | 0.030 (5) | −0.005 (4) |
O6 | 0.053 (6) | 0.125 (9) | 0.045 (5) | 0.035 (6) | 0.005 (4) | −0.006 (5) |
O7 | 0.133 (9) | 0.141 (9) | 0.076 (6) | 0.059 (8) | 0.006 (6) | −0.021 (6) |
O8 | 0.075 (6) | 0.083 (9) | 0.136 (12) | 0.034 (6) | 0.012 (7) | −0.034 (8) |
O9 | 0.202 (12) | 0.168 (10) | 0.234 (13) | −0.059 (9) | 0.075 (10) | −0.006 (8) |
O6' | 0.181 (12) | 0.234 (14) | 0.126 (7) | −0.014 (10) | 0.020 (8) | 0.001 (9) |
O7' | 0.090 (8) | 0.067 (9) | 0.144 (15) | −0.001 (7) | −0.006 (9) | 0.002 (9) |
O8' | 0.25 (3) | 0.172 (16) | 0.28 (3) | 0.12 (2) | 0.20 (3) | 0.066 (19) |
O9' | 0.19 (2) | 0.139 (13) | 0.22 (2) | −0.063 (16) | 0.11 (2) | −0.032 (15) |
Geometric parameters (Å, º) top
Cu1—O3 | 1.889 (5) | N3—C10 | 1.471 (10) |
Cu1—N2 | 1.919 (5) | N3—H3A | 0.91 |
Cu1—O4 | 1.989 (5) | C1—C6 | 1.377 (10) |
Cu1—N3 | 1.991 (5) | C1—C2 | 1.432 (9) |
Cu1—O5 | 2.403 (5) | C1—C7 | 1.456 (9) |
Cl1—O9 | 1.358 (9) | C2—C3 | 1.415 (9) |
Cl1—O9' | 1.365 (10) | C3—C4 | 1.360 (11) |
Cl1—O6' | 1.368 (10) | C3—H3 | 0.93 |
Cl1—O8 | 1.397 (8) | C4—C5 | 1.399 (10) |
Cl1—O7 | 1.401 (9) | C4—H4 | 0.93 |
Cl1—O7' | 1.414 (9) | C5—C6 | 1.380 (9) |
Cl1—O8' | 1.446 (10) | C6—H6 | 0.93 |
Cl1—O6 | 1.473 (8) | C7—H7 | 0.93 |
O1—N1 | 1.225 (9) | C8—C9 | 1.506 (11) |
O2—N1 | 1.217 (8) | C8—H8A | 0.97 |
O3—C2 | 1.287 (8) | C8—H8B | 0.97 |
O4—C11 | 1.440 (10) | C9—H9A | 0.97 |
O4—H4A | 0.93 | C9—H9B | 0.97 |
O5—H5A | 0.84 | C10—C11 | 1.499 (12) |
O5—H5B | 0.84 | C10—H10A | 0.97 |
N1—C5 | 1.441 (9) | C10—H10B | 0.97 |
N2—C7 | 1.259 (9) | C11—H11A | 0.97 |
N2—C8 | 1.476 (8) | C11—H11B | 0.97 |
N3—C9 | 1.466 (9) | | |
| | | |
O3—Cu1—N2 | 95.1 (2) | C9—N3—C10 | 115.4 (6) |
O3—Cu1—O4 | 94.9 (2) | C9—N3—Cu1 | 106.6 (4) |
N2—Cu1—O4 | 161.3 (2) | C10—N3—Cu1 | 108.9 (4) |
O3—Cu1—N3 | 174.0 (2) | C9—N3—H3A | 108.6 |
N2—Cu1—N3 | 85.1 (2) | C10—N3—H3A | 108.6 |
O4—Cu1—N3 | 83.3 (2) | Cu1—N3—H3A | 108.6 |
O3—Cu1—O5 | 90.9 (2) | C6—C1—C2 | 120.2 (6) |
N2—Cu1—O5 | 102.8 (2) | C6—C1—C7 | 117.3 (6) |
O4—Cu1—O5 | 92.8 (2) | C2—C1—C7 | 122.5 (6) |
N3—Cu1—O5 | 94.8 (2) | O3—C2—C3 | 119.0 (6) |
O9—Cl1—O9' | 162.3 (12) | O3—C2—C1 | 124.8 (6) |
O9—Cl1—O6' | 77.3 (12) | C3—C2—C1 | 116.2 (6) |
O9'—Cl1—O6' | 119.2 (10) | C4—C3—C2 | 123.2 (6) |
O9—Cl1—O8 | 115.0 (9) | C4—C3—H3 | 118.4 |
O9'—Cl1—O8 | 75.1 (11) | C2—C3—H3 | 118.4 |
O6'—Cl1—O8 | 85.1 (11) | C3—C4—C5 | 119.1 (6) |
O9—Cl1—O7 | 114.1 (9) | C3—C4—H4 | 120.5 |
O9'—Cl1—O7 | 48.3 (10) | C5—C4—H4 | 120.5 |
O6'—Cl1—O7 | 153.2 (12) | C6—C5—C4 | 120.1 (7) |
O8—Cl1—O7 | 109.2 (8) | C6—C5—N1 | 120.5 (6) |
O9—Cl1—O7' | 53.2 (10) | C4—C5—N1 | 119.4 (6) |
O9'—Cl1—O7' | 111.5 (10) | C1—C6—C5 | 121.2 (6) |
O6'—Cl1—O7' | 109.6 (9) | C1—C6—H6 | 119.4 |
O8—Cl1—O7' | 155.6 (8) | C5—C6—H6 | 119.4 |
O7—Cl1—O7' | 66.3 (9) | N2—C7—C1 | 125.2 (6) |
O9—Cl1—O8' | 71.1 (11) | N2—C7—H7 | 117.4 |
O9'—Cl1—O8' | 107.0 (9) | C1—C7—H7 | 117.4 |
O6'—Cl1—O8' | 107.0 (10) | N2—C8—C9 | 107.1 (6) |
O8—Cl1—O8' | 55.5 (10) | N2—C8—H8A | 110.3 |
O7—Cl1—O8' | 99.7 (11) | C9—C8—H8A | 110.3 |
O7'—Cl1—O8' | 100.7 (9) | N2—C8—H8B | 110.3 |
O9—Cl1—O6 | 109.5 (9) | C9—C8—H8B | 110.3 |
O9'—Cl1—O6 | 80.5 (10) | H8A—C8—H8B | 108.6 |
O6'—Cl1—O6 | 49.1 (11) | N3—C9—C8 | 107.7 (6) |
O8—Cl1—O6 | 103.4 (6) | N3—C9—H9A | 110.2 |
O7—Cl1—O6 | 104.5 (7) | C8—C9—H9A | 110.2 |
O7'—Cl1—O6 | 100.9 (8) | N3—C9—H9B | 110.2 |
O8'—Cl1—O6 | 152.5 (10) | C8—C9—H9B | 110.2 |
C2—O3—Cu1 | 126.3 (4) | H9A—C9—H9B | 108.5 |
C11—O4—Cu1 | 111.5 (4) | N3—C10—C11 | 107.5 (6) |
C11—O4—H4A | 124.3 | N3—C10—H10A | 110.2 |
Cu1—O4—H4A | 124.3 | C11—C10—H10A | 110.2 |
Cu1—O5—H5A | 96.5 | N3—C10—H10B | 110.2 |
Cu1—O5—H5B | 114.0 | C11—C10—H10B | 110.2 |
H5A—O5—H5B | 108.9 | H10A—C10—H10B | 108.5 |
O2—N1—O1 | 122.6 (7) | O4—C11—C10 | 106.9 (7) |
O2—N1—C5 | 119.1 (7) | O4—C11—H11A | 110.3 |
O1—N1—C5 | 118.3 (6) | C10—C11—H11A | 110.3 |
C7—N2—C8 | 121.5 (6) | O4—C11—H11B | 110.3 |
C7—N2—Cu1 | 125.8 (4) | C10—C11—H11B | 110.3 |
C8—N2—Cu1 | 112.6 (5) | H11A—C11—H11B | 108.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O5i | 0.93 | 1.98 | 2.795 (7) | 145 |
N3—H3A···O6′ii | 0.91 | 2.04 | 2.854 (19) | 148 |
N3—H3A···O6ii | 0.91 | 2.16 | 3.047 (10) | 164 |
O5—H5A···O8ii | 0.84 | 1.98 | 2.811 (14) | 169 |
O5—H5A···O9′ii | 0.84 | 2.39 | 3.01 (2) | 131 |
O5—H5B···O2iii | 0.84 | 2.27 | 3.029 (8) | 152 |
O5—H5B···O1iii | 0.84 | 2.58 | 3.055 (8) | 117 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y, z+1/2; (iii) −x, −y+1, −z+1. |