The molecule of the title complex, [Cu(C
15H
11N
2O
2)
2(H
2O)
2], lies on a twofold rotation axis. The crystal structure is based on a network of intermolecular N—H
O=C and O—H
O=C interactions.
Supporting information
CCDC reference: 299884
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.007 Å
- R factor = 0.050
- wR factor = 0.136
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.89 Ratio
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O3 .. 7.51 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O4 .. 8.44 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 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
6 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.
trans-Diaquabis(5,5-diphenylhydantoinato-
κN3)copper(II)
top
Crystal data top
| [Cu(C15H11N2O2)2(H2O)2] | F(000) = 1244 |
| Mr = 602.09 | Dx = 1.383 Mg m−3 |
| Monoclinic, C2/c | Melting point: 508 K |
| Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
| a = 31.341 (7) Å | Cell parameters from 1879 reflections |
| b = 8.5690 (19) Å | θ = 2.5–25.4° |
| c = 11.287 (3) Å | µ = 0.80 mm−1 |
| β = 107.411 (4)° | T = 298 K |
| V = 2892.4 (11) Å3 | Block, violet-red |
| Z = 4 | 0.33 × 0.15 × 0.05 mm |
Data collection top
Bruker SMART CCD area-detector
diffractometer | 2544 independent reflections |
| Radiation source: fine-focus sealed tube | 1861 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.039 |
| φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996) | h = −37→29 |
| Tmin = 0.777, Tmax = 0.961 | k = −10→9 |
| 7319 measured reflections | l = −13→13 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.136 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.078P)2 + 1.2445P]
where P = (Fo2 + 2Fc2)/3 |
| 2544 reflections | (Δ/σ)max < 0.001 |
| 187 parameters | Δρmax = 0.36 e Å−3 |
| 0 restraints | Δρmin = −0.44 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| Cu1 | 0.5000 | 0.46965 (7) | 0.2500 | 0.0375 (2) | |
| N1 | 0.55046 (9) | 0.4708 (3) | 0.4070 (2) | 0.0356 (7) | |
| N2 | 0.58208 (11) | 0.4430 (3) | 0.6118 (3) | 0.0456 (8) | |
| H2 | 0.5861 | 0.4110 | 0.6866 | 0.055* | |
| O1 | 0.59771 (8) | 0.6536 (3) | 0.3655 (2) | 0.0443 (6) | |
| O2 | 0.52087 (9) | 0.2945 (3) | 0.5163 (2) | 0.0481 (6) | |
| O3 | 0.5000 | 0.2384 (5) | 0.2500 | 0.0910 (16) | |
| H16 | 0.5067 | 0.1813 | 0.1967 | 0.109* | |
| O4 | 0.5000 | 0.7038 (5) | 0.2500 | 0.0642 (11) | |
| H17 | 0.5101 | 0.7589 | 0.2019 | 0.077* | |
| C2 | 0.58579 (11) | 0.5679 (4) | 0.4374 (3) | 0.0364 (8) | |
| C1 | 0.54839 (12) | 0.3941 (4) | 0.5131 (3) | 0.0352 (8) | |
| C3 | 0.61070 (11) | 0.5556 (4) | 0.5770 (3) | 0.0364 (8) | |
| C4 | 0.65814 (14) | 0.4952 (5) | 0.5956 (4) | 0.0511 (10) | |
| C5 | 0.67226 (18) | 0.3547 (6) | 0.6537 (5) | 0.0823 (15) | |
| H5 | 0.6530 | 0.2953 | 0.6839 | 0.099* | |
| C6 | 0.7151 (3) | 0.3024 (10) | 0.6668 (7) | 0.132 (3) | |
| H6 | 0.7248 | 0.2082 | 0.7068 | 0.158* | |
| C7 | 0.7430 (2) | 0.3872 (13) | 0.6220 (9) | 0.137 (4) | |
| H7 | 0.7715 | 0.3499 | 0.6298 | 0.164* | |
| C8 | 0.7299 (2) | 0.5263 (10) | 0.5656 (7) | 0.118 (2) | |
| H8 | 0.7493 | 0.5846 | 0.5351 | 0.141* | |
| C9 | 0.68751 (16) | 0.5800 (7) | 0.5540 (5) | 0.0814 (15) | |
| H9 | 0.6787 | 0.6765 | 0.5169 | 0.098* | |
| C10 | 0.61117 (11) | 0.7095 (4) | 0.6463 (3) | 0.0369 (8) | |
| C11 | 0.63263 (14) | 0.7135 (5) | 0.7718 (3) | 0.0509 (10) | |
| H11 | 0.6476 | 0.6251 | 0.8109 | 0.061* | |
| C12 | 0.63232 (15) | 0.8469 (5) | 0.8412 (4) | 0.0622 (12) | |
| H12 | 0.6465 | 0.8465 | 0.9263 | 0.075* | |
| C13 | 0.61159 (17) | 0.9770 (5) | 0.7856 (5) | 0.0694 (13) | |
| H13 | 0.6120 | 1.0673 | 0.8318 | 0.083* | |
| C14 | 0.58988 (19) | 0.9755 (5) | 0.6610 (5) | 0.0760 (15) | |
| H14 | 0.5753 | 1.0648 | 0.6226 | 0.091* | |
| C15 | 0.58951 (15) | 0.8422 (4) | 0.5916 (4) | 0.0580 (11) | |
| H15 | 0.5744 | 0.8425 | 0.5071 | 0.070* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Cu1 | 0.0421 (4) | 0.0382 (4) | 0.0282 (3) | 0.000 | 0.0042 (3) | 0.000 |
| N1 | 0.0391 (17) | 0.0398 (15) | 0.0272 (15) | −0.0008 (14) | 0.0087 (12) | 0.0006 (12) |
| N2 | 0.064 (2) | 0.0442 (18) | 0.0246 (15) | −0.0096 (16) | 0.0071 (14) | 0.0061 (13) |
| O1 | 0.0551 (16) | 0.0489 (15) | 0.0279 (13) | −0.0100 (12) | 0.0110 (11) | 0.0011 (11) |
| O2 | 0.0524 (16) | 0.0540 (16) | 0.0379 (14) | −0.0112 (14) | 0.0135 (12) | 0.0038 (12) |
| O3 | 0.131 (5) | 0.066 (3) | 0.061 (3) | 0.000 | 0.007 (3) | 0.000 |
| O4 | 0.077 (3) | 0.061 (3) | 0.054 (2) | 0.000 | 0.018 (2) | 0.000 |
| C2 | 0.039 (2) | 0.042 (2) | 0.0262 (18) | 0.0050 (16) | 0.0064 (15) | 0.0008 (15) |
| C1 | 0.039 (2) | 0.0385 (19) | 0.0260 (17) | 0.0069 (17) | 0.0065 (15) | 0.0018 (15) |
| C3 | 0.040 (2) | 0.038 (2) | 0.0262 (17) | 0.0019 (16) | 0.0029 (14) | 0.0027 (14) |
| C4 | 0.047 (2) | 0.059 (3) | 0.040 (2) | 0.004 (2) | 0.0015 (17) | −0.0161 (18) |
| C5 | 0.074 (3) | 0.080 (4) | 0.079 (4) | 0.031 (3) | 0.002 (3) | 0.001 (3) |
| C6 | 0.115 (6) | 0.129 (6) | 0.122 (6) | 0.075 (5) | −0.008 (5) | −0.008 (5) |
| C7 | 0.065 (5) | 0.182 (9) | 0.149 (8) | 0.042 (5) | 0.010 (5) | −0.054 (7) |
| C8 | 0.054 (4) | 0.166 (7) | 0.134 (6) | −0.001 (4) | 0.029 (4) | −0.033 (5) |
| C9 | 0.051 (3) | 0.098 (4) | 0.093 (4) | 0.001 (3) | 0.017 (3) | −0.015 (3) |
| C10 | 0.040 (2) | 0.039 (2) | 0.0308 (18) | −0.0023 (16) | 0.0079 (15) | −0.0009 (15) |
| C11 | 0.064 (3) | 0.046 (2) | 0.035 (2) | 0.0001 (19) | 0.0035 (18) | −0.0041 (17) |
| C12 | 0.081 (3) | 0.058 (3) | 0.042 (2) | −0.005 (2) | 0.010 (2) | −0.015 (2) |
| C13 | 0.093 (4) | 0.050 (3) | 0.068 (3) | −0.003 (3) | 0.029 (3) | −0.019 (2) |
| C14 | 0.107 (4) | 0.046 (3) | 0.074 (3) | 0.021 (3) | 0.025 (3) | 0.004 (2) |
| C15 | 0.081 (3) | 0.046 (2) | 0.042 (2) | 0.010 (2) | 0.011 (2) | 0.0020 (18) |
Geometric parameters (Å, º) top
| Cu1—N1 | 1.991 (3) | C5—H5 | 0.9300 |
| Cu1—N1i | 1.991 (3) | C6—C7 | 1.345 (11) |
| Cu1—O3 | 1.982 (5) | C6—H6 | 0.9300 |
| Cu1—O4 | 2.006 (4) | C7—C8 | 1.356 (11) |
| N1—C2 | 1.345 (4) | C7—H7 | 0.9300 |
| N1—C1 | 1.384 (4) | C8—C9 | 1.374 (8) |
| N2—C1 | 1.352 (4) | C8—H8 | 0.9300 |
| N2—C3 | 1.450 (4) | C9—H9 | 0.9300 |
| N2—H2 | 0.8600 | C10—C15 | 1.373 (5) |
| O1—C2 | 1.232 (4) | C10—C11 | 1.374 (5) |
| O2—C1 | 1.221 (4) | C11—C12 | 1.388 (5) |
| O3—H16 | 0.8498 | C11—H11 | 0.9300 |
| O4—H17 | 0.8497 | C12—C13 | 1.347 (6) |
| C2—C3 | 1.539 (4) | C12—H12 | 0.9300 |
| C3—C4 | 1.528 (5) | C13—C14 | 1.367 (7) |
| C3—C10 | 1.531 (5) | C13—H13 | 0.9300 |
| C4—C9 | 1.363 (7) | C14—C15 | 1.383 (6) |
| C4—C5 | 1.378 (6) | C14—H14 | 0.9300 |
| C5—C6 | 1.382 (8) | C15—H15 | 0.9300 |
| | | |
| N1—Cu1—O3 | 90.28 (8) | C6—C5—H5 | 120.1 |
| N1—Cu1—O4 | 89.72 (8) | C7—C6—C5 | 120.2 (7) |
| N1i—Cu1—N1 | 179.44 (16) | C7—C6—H6 | 119.9 |
| O3—Cu1—O4 | 180.000 (1) | C5—C6—H6 | 119.9 |
| N1i—Cu1—O3 | 90.28 (8) | C6—C7—C8 | 120.8 (7) |
| N1i—Cu1—O4 | 89.72 (8) | C6—C7—H7 | 119.6 |
| C2—N1—Cu1 | 127.2 (2) | C8—C7—H7 | 119.6 |
| C1—N1—Cu1 | 122.5 (2) | C7—C8—C9 | 119.2 (7) |
| C2—N1—C1 | 108.7 (3) | C7—C8—H8 | 120.4 |
| C1—N2—C3 | 112.1 (3) | C9—C8—H8 | 120.4 |
| C1—N2—H2 | 123.9 | C4—C9—C8 | 121.4 (6) |
| C3—N2—H2 | 123.9 | C4—C9—H9 | 119.3 |
| Cu1—O3—H16 | 125.2 | C8—C9—H9 | 119.3 |
| Cu1—O4—H17 | 123.8 | C15—C10—C11 | 117.8 (3) |
| O1—C2—N1 | 126.1 (3) | C15—C10—C3 | 123.8 (3) |
| O1—C2—C3 | 123.7 (3) | C11—C10—C3 | 118.4 (3) |
| N1—C2—C3 | 110.2 (3) | C10—C11—C12 | 121.2 (4) |
| O2—C1—N2 | 125.2 (3) | C10—C11—H11 | 119.4 |
| O2—C1—N1 | 125.0 (3) | C12—C11—H11 | 119.4 |
| N2—C1—N1 | 109.8 (3) | C13—C12—C11 | 120.2 (4) |
| N2—C3—C4 | 113.1 (3) | C13—C12—H12 | 119.9 |
| N2—C3—C10 | 110.3 (3) | C11—C12—H12 | 119.9 |
| C4—C3—C10 | 111.2 (3) | C12—C13—C14 | 119.6 (4) |
| N2—C3—C2 | 99.1 (3) | C12—C13—H13 | 120.2 |
| C4—C3—C2 | 109.8 (3) | C14—C13—H13 | 120.2 |
| C10—C3—C2 | 112.9 (3) | C13—C14—C15 | 120.5 (4) |
| C9—C4—C5 | 118.4 (4) | C13—C14—H14 | 119.8 |
| C9—C4—C3 | 120.1 (4) | C15—C14—H14 | 119.8 |
| C5—C4—C3 | 121.5 (4) | C10—C15—C14 | 120.7 (4) |
| C4—C5—C6 | 119.9 (6) | C10—C15—H15 | 119.7 |
| C4—C5—H5 | 120.1 | C14—C15—H15 | 119.7 |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1ii | 0.86 | 2.02 | 2.878 (4) | 177 |
| O3—H16···O2i | 0.85 | 2.49 | 2.918 (3) | 112 |
| O4—H17···O2iii | 0.85 | 2.27 | 2.902 (2) | 132 |
| Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+1, z+1/2; (iii) x, −y+1, z−1/2. |
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metal-organic compounds
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.007 Å
Alert level B
Alert level C
