The title compound, [Cd(C
11H
5N
2O
2)
2(H
2O)
2], is a mononuclear complex consisting of a Cd
II atom, two 3-hydroxy-4,5-diazafluoren-9-one ligands and two coordinated water molecules. The Cd
II atom, lying on a twofold axis, displays a distorted octahedral coordintion. Adjacent molecules are linked by O—H

O hydrogen bonds and π–π interactions [centroid–centroid distance = 3.84 (1) Å], leading to a one-dimensional chain. Weak C—H

O hydrogen bonds connect the chains into a two-dimensional supramolecular structure.
Supporting information
CCDC reference: 677384
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.029
- wR factor = 0.082
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
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Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Cadmium(II) acetate dihydrate (0.080 g, 0.3 mmol),
3-hydroxyl-4,5-diazafluoren-9-one (0.040 g, 0.2 mmol), sodium hydroxide (0.024 g, 0.4 mmol) and water (14 ml) were placed in a 23 ml Teflon-lined autoclave,
which was heated at 423 K for 3 d. After cooling slowly to room temperature at
a rate of 10 K h-1, colorless crystals of the title compound were obtained.
Analysis calculated for C22H14CdN4O6: C 48.64, H 2.58, N 10.32%;
found: C 48.51, H 2.67, N 10.42%.
H atoms on C atoms were positioned geometrically and refined as riding, with
C—H = 0.93Å and Uiso(H) = 1.2Ueq(C). H atoms of water
molecule were located on a difference Fourier map and refined isotropically
with a restraint of O—H = 0.82 (1) Å.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Diaquabis(9-oxo-4,5-diazafluoren-3-olato-
κ2N4,
O3)cadmium(II)
top
Crystal data top
[Cd(C11H5N2O2)2(H2O)2] | F(000) = 1080 |
Mr = 542.77 | Dx = 1.760 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4465 reflections |
a = 28.190 (5) Å | θ = 3.0–28.3° |
b = 5.572 (4) Å | µ = 1.12 mm−1 |
c = 13.933 (5) Å | T = 293 K |
β = 110.622 (5)° | Block, colorless |
V = 2048.3 (17) Å3 | 0.26 × 0.21 × 0.17 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2406 independent reflections |
Radiation source: rotation anode | 1965 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 28.3°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −26→37 |
Tmin = 0.760, Tmax = 0.833 | k = −7→7 |
5972 measured reflections | l = −18→12 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0433P)2 + 1.5483P] where P = (Fo2 + 2Fc2)/3 |
2406 reflections | (Δ/σ)max < 0.001 |
158 parameters | Δρmax = 0.62 e Å−3 |
2 restraints | Δρmin = −0.36 e Å−3 |
Crystal data top
[Cd(C11H5N2O2)2(H2O)2] | V = 2048.3 (17) Å3 |
Mr = 542.77 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 28.190 (5) Å | µ = 1.12 mm−1 |
b = 5.572 (4) Å | T = 293 K |
c = 13.933 (5) Å | 0.26 × 0.21 × 0.17 mm |
β = 110.622 (5)° | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2406 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1965 reflections with I > 2σ(I) |
Tmin = 0.760, Tmax = 0.833 | Rint = 0.021 |
5972 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.029 | 2 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.62 e Å−3 |
2406 reflections | Δρmin = −0.36 e Å−3 |
158 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 1.0000 | 0.24267 (5) | 0.2500 | 0.04153 (11) | |
N1 | 0.91692 (7) | 0.1412 (4) | 0.15373 (15) | 0.0337 (4) | |
N2 | 0.90481 (8) | 0.5376 (4) | −0.00770 (16) | 0.0400 (5) | |
O2 | 0.95401 (7) | −0.0756 (3) | 0.29552 (14) | 0.0455 (4) | |
O3 | 0.75172 (7) | 0.0883 (4) | −0.09790 (15) | 0.0553 (5) | |
C1 | 0.91486 (9) | −0.0461 (4) | 0.21600 (18) | 0.0358 (5) | |
C2 | 0.87029 (11) | −0.1903 (5) | 0.1904 (2) | 0.0430 (6) | |
H2 | 0.8695 | −0.3203 | 0.2317 | 0.052* | |
C3 | 0.82874 (10) | −0.1395 (5) | 0.1061 (2) | 0.0423 (6) | |
H3 | 0.7995 | −0.2322 | 0.0897 | 0.051* | |
C4 | 0.83130 (9) | 0.0555 (5) | 0.04508 (18) | 0.0366 (5) | |
C5 | 0.79449 (9) | 0.1567 (5) | −0.0489 (2) | 0.0404 (6) | |
C6 | 0.82108 (9) | 0.3654 (5) | −0.07684 (18) | 0.0377 (5) | |
C7 | 0.80569 (10) | 0.5278 (5) | −0.1560 (2) | 0.0470 (6) | |
H7 | 0.7731 | 0.5249 | −0.2045 | 0.056* | |
C8 | 0.84113 (12) | 0.6963 (5) | −0.1601 (2) | 0.0501 (7) | |
H8 | 0.8325 | 0.8102 | −0.2122 | 0.060* | |
C9 | 0.88918 (12) | 0.6950 (5) | −0.0868 (2) | 0.0460 (7) | |
H9 | 0.9122 | 0.8091 | −0.0920 | 0.055* | |
C10 | 0.87021 (9) | 0.3786 (4) | −0.00494 (17) | 0.0334 (5) | |
C11 | 0.87612 (9) | 0.1865 (4) | 0.07194 (19) | 0.0327 (5) | |
O1 | 0.99406 (8) | 0.4960 (4) | 0.36946 (16) | 0.0505 (5) | |
H1A | 1.0223 (8) | 0.519 (6) | 0.412 (2) | 0.065 (10)* | |
H1B | 0.9809 (13) | 0.630 (4) | 0.353 (3) | 0.067 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.02980 (15) | 0.03837 (17) | 0.04841 (18) | 0.000 | 0.00383 (11) | 0.000 |
N1 | 0.0281 (10) | 0.0314 (10) | 0.0377 (11) | −0.0028 (8) | 0.0066 (8) | 0.0013 (9) |
N2 | 0.0387 (11) | 0.0401 (12) | 0.0400 (11) | −0.0032 (9) | 0.0125 (9) | 0.0036 (9) |
O2 | 0.0427 (10) | 0.0407 (10) | 0.0454 (10) | 0.0028 (8) | 0.0058 (8) | 0.0076 (8) |
O3 | 0.0343 (10) | 0.0707 (14) | 0.0495 (11) | −0.0142 (9) | 0.0005 (8) | −0.0081 (10) |
C1 | 0.0369 (12) | 0.0317 (12) | 0.0382 (13) | 0.0023 (10) | 0.0124 (10) | 0.0002 (10) |
C2 | 0.0489 (16) | 0.0348 (13) | 0.0490 (15) | −0.0056 (11) | 0.0218 (13) | 0.0017 (11) |
C3 | 0.0385 (14) | 0.0400 (14) | 0.0494 (15) | −0.0123 (11) | 0.0168 (12) | −0.0068 (12) |
C4 | 0.0296 (11) | 0.0403 (13) | 0.0385 (13) | −0.0051 (10) | 0.0103 (10) | −0.0061 (11) |
C5 | 0.0331 (13) | 0.0464 (14) | 0.0396 (13) | −0.0031 (11) | 0.0100 (11) | −0.0089 (12) |
C6 | 0.0317 (12) | 0.0444 (15) | 0.0345 (12) | −0.0003 (10) | 0.0085 (10) | −0.0048 (11) |
C7 | 0.0415 (14) | 0.0581 (17) | 0.0355 (13) | 0.0076 (12) | 0.0062 (11) | 0.0035 (12) |
C8 | 0.0597 (18) | 0.0509 (16) | 0.0383 (14) | 0.0123 (14) | 0.0154 (13) | 0.0101 (12) |
C9 | 0.0500 (16) | 0.0423 (15) | 0.0499 (16) | 0.0011 (12) | 0.0227 (13) | 0.0083 (12) |
C10 | 0.0318 (11) | 0.0350 (13) | 0.0312 (11) | −0.0004 (9) | 0.0086 (9) | −0.0022 (10) |
C11 | 0.0296 (12) | 0.0320 (12) | 0.0353 (12) | −0.0025 (9) | 0.0097 (10) | −0.0030 (10) |
O1 | 0.0448 (12) | 0.0426 (11) | 0.0532 (12) | 0.0076 (9) | 0.0039 (10) | −0.0025 (10) |
Geometric parameters (Å, º) top
Cd1—O1 | 2.233 (2) | C3—C4 | 1.397 (4) |
Cd1—O1i | 2.233 (2) | C3—H3 | 0.9300 |
Cd1—N1i | 2.3217 (19) | C4—C11 | 1.391 (3) |
Cd1—N1 | 2.3217 (19) | C4—C5 | 1.468 (4) |
Cd1—O2 | 2.410 (2) | C5—C6 | 1.507 (4) |
Cd1—O2i | 2.410 (2) | C6—C7 | 1.374 (4) |
N1—C11 | 1.327 (3) | C6—C10 | 1.396 (3) |
N1—C1 | 1.371 (3) | C7—C8 | 1.386 (4) |
N2—C10 | 1.328 (3) | C7—H7 | 0.9300 |
N2—C9 | 1.355 (3) | C8—C9 | 1.380 (4) |
O2—C1 | 1.269 (3) | C8—H8 | 0.9300 |
O3—C5 | 1.219 (3) | C9—H9 | 0.9300 |
C1—C2 | 1.427 (4) | C10—C11 | 1.482 (4) |
C2—C3 | 1.365 (4) | O1—H1A | 0.817 (18) |
C2—H2 | 0.9300 | O1—H1B | 0.832 (19) |
| | | |
O1—Cd1—O1i | 101.59 (13) | C4—C3—H3 | 120.9 |
O1—Cd1—N1i | 92.77 (7) | C11—C4—C3 | 118.8 (2) |
O1i—Cd1—N1i | 105.03 (8) | C11—C4—C5 | 109.1 (2) |
O1—Cd1—N1 | 105.03 (8) | C3—C4—C5 | 132.1 (2) |
O1i—Cd1—N1 | 92.77 (7) | O3—C5—C4 | 128.9 (3) |
N1i—Cd1—N1 | 151.82 (11) | O3—C5—C6 | 125.5 (3) |
O1—Cd1—O2 | 94.62 (9) | C4—C5—C6 | 105.5 (2) |
O1i—Cd1—O2 | 148.19 (7) | C7—C6—C10 | 119.6 (2) |
N1i—Cd1—O2 | 101.27 (7) | C7—C6—C5 | 132.1 (2) |
N1—Cd1—O2 | 56.38 (7) | C10—C6—C5 | 108.3 (2) |
O1—Cd1—O2i | 148.19 (7) | C6—C7—C8 | 116.8 (2) |
O1i—Cd1—O2i | 94.62 (9) | C6—C7—H7 | 121.6 |
N1i—Cd1—O2i | 56.38 (7) | C8—C7—H7 | 121.6 |
N1—Cd1—O2i | 101.27 (7) | C9—C8—C7 | 120.0 (3) |
O2—Cd1—O2i | 85.23 (11) | C9—C8—H8 | 120.0 |
C11—N1—C1 | 118.1 (2) | C7—C8—H8 | 120.0 |
C11—N1—Cd1 | 147.41 (17) | N2—C9—C8 | 124.0 (3) |
C1—N1—Cd1 | 94.51 (14) | N2—C9—H9 | 118.0 |
C10—N2—C9 | 115.1 (2) | C8—C9—H9 | 118.0 |
C1—O2—Cd1 | 93.31 (15) | N2—C10—C6 | 124.6 (2) |
O2—C1—N1 | 115.7 (2) | N2—C10—C11 | 127.3 (2) |
O2—C1—C2 | 124.3 (2) | C6—C10—C11 | 108.1 (2) |
N1—C1—C2 | 120.0 (2) | N1—C11—C4 | 124.2 (2) |
C3—C2—C1 | 120.8 (3) | N1—C11—C10 | 126.9 (2) |
C3—C2—H2 | 119.6 | C4—C11—C10 | 108.9 (2) |
C1—C2—H2 | 119.6 | Cd1—O1—H1A | 109 (2) |
C2—C3—C4 | 118.2 (2) | Cd1—O1—H1B | 120 (2) |
C2—C3—H3 | 120.9 | H1A—O1—H1B | 107 (3) |
| | | |
O1—Cd1—N1—C11 | 93.5 (3) | C3—C4—C5—C6 | −179.4 (3) |
O1i—Cd1—N1—C11 | −9.3 (3) | O3—C5—C6—C7 | 2.3 (5) |
N1i—Cd1—N1—C11 | −139.1 (3) | C4—C5—C6—C7 | −179.5 (3) |
O2—Cd1—N1—C11 | 179.0 (3) | O3—C5—C6—C10 | −176.9 (3) |
O2i—Cd1—N1—C11 | −104.6 (3) | C4—C5—C6—C10 | 1.4 (3) |
O1—Cd1—N1—C1 | −87.51 (16) | C10—C6—C7—C8 | 0.9 (4) |
O1i—Cd1—N1—C1 | 169.70 (14) | C5—C6—C7—C8 | −178.2 (3) |
N1i—Cd1—N1—C1 | 39.89 (13) | C6—C7—C8—C9 | 0.1 (4) |
O2—Cd1—N1—C1 | −2.01 (13) | C10—N2—C9—C8 | 0.3 (4) |
O2i—Cd1—N1—C1 | 74.44 (15) | C7—C8—C9—N2 | −0.7 (5) |
O1—Cd1—O2—C1 | 107.16 (15) | C9—N2—C10—C6 | 0.7 (4) |
O1i—Cd1—O2—C1 | −13.7 (2) | C9—N2—C10—C11 | −179.8 (2) |
N1i—Cd1—O2—C1 | −159.08 (14) | C7—C6—C10—N2 | −1.3 (4) |
N1—Cd1—O2—C1 | 2.17 (14) | C5—C6—C10—N2 | 178.0 (2) |
O2i—Cd1—O2—C1 | −104.75 (16) | C7—C6—C10—C11 | 179.0 (2) |
Cd1—O2—C1—N1 | −3.4 (2) | C5—C6—C10—C11 | −1.7 (3) |
Cd1—O2—C1—C2 | 177.7 (2) | C1—N1—C11—C4 | −0.2 (4) |
C11—N1—C1—O2 | −177.1 (2) | Cd1—N1—C11—C4 | 178.7 (2) |
Cd1—N1—C1—O2 | 3.5 (2) | C1—N1—C11—C10 | −180.0 (2) |
C11—N1—C1—C2 | 1.9 (3) | Cd1—N1—C11—C10 | −1.1 (5) |
Cd1—N1—C1—C2 | −177.5 (2) | C3—C4—C11—N1 | −1.3 (4) |
O2—C1—C2—C3 | 176.7 (2) | C5—C4—C11—N1 | 179.7 (2) |
N1—C1—C2—C3 | −2.2 (4) | C3—C4—C11—C10 | 178.6 (2) |
C1—C2—C3—C4 | 0.7 (4) | C5—C4—C11—C10 | −0.5 (3) |
C2—C3—C4—C11 | 0.9 (4) | N2—C10—C11—N1 | 1.6 (4) |
C2—C3—C4—C5 | 179.7 (3) | C6—C10—C11—N1 | −178.8 (2) |
C11—C4—C5—O3 | 177.7 (3) | N2—C10—C11—C4 | −178.3 (2) |
C3—C4—C5—O3 | −1.2 (5) | C6—C10—C11—C4 | 1.4 (3) |
C11—C4—C5—C6 | −0.5 (3) | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2i | 0.82 (2) | 2.02 (2) | 2.832 (3) | 172 (3) |
O1—H1B···O2ii | 0.83 (2) | 1.86 (2) | 2.686 (3) | 170 (4) |
C3—H3···O3iii | 0.93 | 2.48 | 3.351 (5) | 156 |
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) x, y+1, z; (iii) −x+3/2, −y−1/2, −z. |
Experimental details
Crystal data |
Chemical formula | [Cd(C11H5N2O2)2(H2O)2] |
Mr | 542.77 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 28.190 (5), 5.572 (4), 13.933 (5) |
β (°) | 110.622 (5) |
V (Å3) | 2048.3 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.12 |
Crystal size (mm) | 0.26 × 0.21 × 0.17 |
|
Data collection |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.760, 0.833 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5972, 2406, 1965 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.667 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.082, 1.02 |
No. of reflections | 2406 |
No. of parameters | 158 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.62, −0.36 |
Selected geometric parameters (Å, º) topCd1—O1 | 2.233 (2) | Cd1—O2 | 2.410 (2) |
Cd1—N1 | 2.3217 (19) | | |
| | | |
O1—Cd1—O1i | 101.59 (13) | O1i—Cd1—O2 | 148.19 (7) |
O1—Cd1—N1i | 92.77 (7) | N1i—Cd1—O2 | 101.27 (7) |
O1—Cd1—N1 | 105.03 (8) | N1—Cd1—O2 | 56.38 (7) |
N1i—Cd1—N1 | 151.82 (11) | O2—Cd1—O2i | 85.23 (11) |
O1—Cd1—O2 | 94.62 (9) | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N2i | 0.82 (2) | 2.02 (2) | 2.832 (3) | 172 (3) |
O1—H1B···O2ii | 0.83 (2) | 1.86 (2) | 2.686 (3) | 170 (4) |
C3—H3···O3iii | 0.93 | 2.48 | 3.351 (5) | 156 |
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) x, y+1, z; (iii) −x+3/2, −y−1/2, −z. |
The structures of 4,5-diazafluoren-9-one and its metal complexes have been reported (Li et al., 2006; Rillema et al., 2007; Tershansy et al., 2006; Zhao et al., 2006). However, no studies of its derivative, 3-hydroxyl-4,5-diazafluoren-9-one, and any metal complexes of the ligand are known to date. In this paper, we present the crystal structure of the title compound, [Cd(C11H5N2O2)2(H2O)2].
The title compound is a neutral mononuclear complex. The CdII atom is six-coordinate and exhibits a distorted octahedral coordintion geometry, defined by two N atoms and two O atoms from two 3-hydroxyl-4,5-diazafluoren-9-one ligands and two O atoms from two aqua ligands (Fig. 1). The Cd—O distances are in the range of 2.233 (2)–2.410 (2)Å and the Cd—N length is 2.322 (2) Å (Table 1). Adjacent molecules are linked by O—H···O hydrogen bonds and π–π interactions [centroid–centroid distance 3.84 (1) Å], leading to a one-dimensional chain. Weak C—H···O hydrogen bonds connect the chains into a two-dimensional supramolecular structure (Fig. 2; Table 2).