The Cd
II ion of the title mononuclear complex, [Cd(C
12H
9O
2)
2(C
7H
6N
2)
2]·H
2O, lies on a crystallographic twofold rotation axis and is in a distorted trigonal prismatic coordination enivironment, involving four carboxylate O atoms from two chelating naphthaleneacetate ligands and two N atoms from two benzimidazole ligands. In the crystal structure, intermolecular N—H
O hydrogen bonds and π–π stacking interactions give rise to a one-dimensional chain structure. The solvent water molecule also lies on a crystallographic twofold rotation axis.
Supporting information
CCDC reference: 640408
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.023
- wR factor = 0.059
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cd1 - O2 .. 10.06 su
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.26 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cd1 - O1 .. 6.54 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
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
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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, 2004); software used to prepare material for publication: SHELXL97.
Bis[(naphthaleneacetato)(1
H-benzimidazole)]cadmium(II) monohydrate
top
Crystal data top
[Cd(C12H9O2)2(C7H6N2)2]·H2O | F(000) = 1504 |
Mr = 737.08 | Dx = 1.499 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 12987 reflections |
a = 11.8418 (2) Å | θ = 2.0–25.1° |
b = 20.0552 (4) Å | µ = 0.72 mm−1 |
c = 14.3436 (4) Å | T = 273 K |
β = 106.571 (1)° | Prism, colorless |
V = 3264.98 (12) Å3 | 0.32 × 0.26 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker APEX-2 diffractometer | 2873 independent reflections |
Radiation source: fine-focus sealed tube | 2635 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10 pixels mm-1 | θmax = 25.1°, θmin = 2.0° |
ω scans | h = −14→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −23→23 |
Tmin = 0.800, Tmax = 0.871 | l = −16→17 |
13266 measured reflections | |
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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0299P)2 + 1.5269P] where P = (Fo2 + 2Fc2)/3 |
2873 reflections | (Δ/σ)max = 0.001 |
221 parameters | Δρmax = 0.32 e Å−3 |
2 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cd1 | 0.5000 | 0.520475 (10) | 0.2500 | 0.04045 (9) | |
N1 | 0.51505 (14) | 0.45084 (8) | 0.13169 (12) | 0.0424 (4) | |
N2 | 0.46851 (16) | 0.40116 (8) | −0.01153 (12) | 0.0499 (4) | |
O1W | 0.5000 | 0.73516 (16) | 0.2500 | 0.1530 (19) | |
O1 | 0.30474 (13) | 0.54213 (8) | 0.16558 (12) | 0.0567 (4) | |
O2 | 0.38129 (12) | 0.60980 (7) | 0.28649 (10) | 0.0484 (4) | |
C1 | 0.29575 (17) | 0.59040 (10) | 0.21769 (14) | 0.0422 (5) | |
C2 | 0.17927 (18) | 0.62734 (12) | 0.19468 (16) | 0.0514 (5) | |
C3 | 0.15771 (16) | 0.66650 (10) | 0.27766 (15) | 0.0451 (5) | |
C4 | 0.1541 (2) | 0.73452 (12) | 0.27532 (19) | 0.0589 (6) | |
C5 | 0.1320 (2) | 0.77234 (12) | 0.3503 (2) | 0.0660 (7) | |
C6 | 0.1148 (2) | 0.74113 (13) | 0.4289 (2) | 0.0658 (7) | |
C7 | 0.11791 (18) | 0.67123 (12) | 0.43656 (16) | 0.0520 (5) | |
C8 | 0.1019 (2) | 0.63708 (15) | 0.51821 (18) | 0.0655 (7) | |
C9 | 0.1063 (2) | 0.56980 (16) | 0.5240 (2) | 0.0726 (8) | |
C10 | 0.1259 (2) | 0.53211 (13) | 0.4490 (2) | 0.0648 (7) | |
C11 | 0.14142 (18) | 0.56275 (11) | 0.36894 (17) | 0.0516 (5) | |
C12 | 0.13935 (16) | 0.63300 (10) | 0.35963 (15) | 0.0420 (5) | |
C13 | 0.43384 (19) | 0.44139 (10) | 0.04902 (15) | 0.0467 (5) | |
C14 | 0.61163 (17) | 0.41383 (9) | 0.12452 (14) | 0.0401 (4) | |
C15 | 0.72194 (19) | 0.40516 (11) | 0.19043 (17) | 0.0522 (5) | |
C16 | 0.8005 (2) | 0.36522 (12) | 0.1621 (2) | 0.0666 (7) | |
C17 | 0.7711 (3) | 0.33456 (12) | 0.0714 (2) | 0.0713 (7) | |
C18 | 0.6623 (3) | 0.34229 (11) | 0.00601 (19) | 0.0635 (7) | |
C19 | 0.5824 (2) | 0.38263 (9) | 0.03375 (15) | 0.0453 (5) | |
H1W1 | 0.543 (4) | 0.7115 (9) | 0.225 (4) | 0.230* | |
H2 | 0.4270 | 0.3890 | −0.0685 | 0.060* | |
H2A | 0.1752 | 0.6577 | 0.1412 | 0.062* | |
H2B | 0.1161 | 0.5952 | 0.1726 | 0.062* | |
H4 | 0.1668 | 0.7565 | 0.2221 | 0.071* | |
H5A | 0.1291 | 0.8186 | 0.3461 | 0.079* | |
H6 | 0.1007 | 0.7664 | 0.4787 | 0.079* | |
H8 | 0.0880 | 0.6615 | 0.5690 | 0.079* | |
H9A | 0.0961 | 0.5486 | 0.5787 | 0.087* | |
H10 | 0.1283 | 0.4858 | 0.4535 | 0.078* | |
H11 | 0.1538 | 0.5368 | 0.3190 | 0.062* | |
H13 | 0.3595 | 0.4608 | 0.0341 | 0.056* | |
H15 | 0.7418 | 0.4255 | 0.2512 | 0.063* | |
H16 | 0.8752 | 0.3585 | 0.2046 | 0.080* | |
H17 | 0.8268 | 0.3081 | 0.0547 | 0.086* | |
H18 | 0.6428 | 0.3214 | −0.0544 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cd1 | 0.03270 (13) | 0.04385 (13) | 0.04581 (14) | 0.000 | 0.01281 (9) | 0.000 |
N1 | 0.0398 (10) | 0.0435 (9) | 0.0437 (9) | 0.0011 (8) | 0.0116 (8) | 0.0003 (8) |
N2 | 0.0570 (12) | 0.0478 (10) | 0.0412 (10) | −0.0057 (9) | 0.0082 (9) | 0.0003 (8) |
O1W | 0.106 (3) | 0.063 (2) | 0.264 (6) | 0.000 | 0.011 (3) | 0.000 |
O1 | 0.0438 (9) | 0.0623 (9) | 0.0592 (9) | 0.0081 (7) | 0.0070 (7) | −0.0106 (8) |
O2 | 0.0296 (7) | 0.0645 (9) | 0.0486 (8) | 0.0037 (7) | 0.0068 (7) | −0.0031 (7) |
C1 | 0.0323 (11) | 0.0517 (12) | 0.0444 (11) | 0.0021 (9) | 0.0136 (9) | 0.0067 (9) |
C2 | 0.0348 (11) | 0.0677 (14) | 0.0487 (12) | 0.0076 (10) | 0.0072 (9) | 0.0016 (10) |
C3 | 0.0246 (10) | 0.0493 (12) | 0.0586 (13) | 0.0044 (9) | 0.0070 (9) | 0.0010 (10) |
C4 | 0.0443 (13) | 0.0539 (13) | 0.0753 (16) | 0.0016 (11) | 0.0121 (12) | 0.0127 (12) |
C5 | 0.0565 (15) | 0.0439 (13) | 0.0896 (19) | 0.0022 (11) | 0.0079 (14) | −0.0099 (13) |
C6 | 0.0519 (14) | 0.0638 (16) | 0.0763 (17) | 0.0038 (12) | 0.0097 (13) | −0.0254 (14) |
C7 | 0.0324 (11) | 0.0636 (14) | 0.0564 (13) | −0.0016 (10) | 0.0067 (10) | −0.0078 (11) |
C8 | 0.0406 (13) | 0.101 (2) | 0.0539 (14) | −0.0058 (14) | 0.0120 (11) | −0.0085 (14) |
C9 | 0.0435 (14) | 0.101 (2) | 0.0703 (17) | −0.0136 (15) | 0.0108 (12) | 0.0233 (16) |
C10 | 0.0425 (14) | 0.0629 (15) | 0.0850 (19) | −0.0055 (11) | 0.0118 (13) | 0.0156 (14) |
C11 | 0.0343 (11) | 0.0509 (12) | 0.0676 (14) | −0.0013 (10) | 0.0114 (10) | 0.0000 (11) |
C12 | 0.0239 (10) | 0.0476 (11) | 0.0524 (12) | −0.0010 (8) | 0.0074 (9) | −0.0034 (9) |
C13 | 0.0434 (12) | 0.0461 (12) | 0.0494 (12) | −0.0007 (10) | 0.0114 (10) | 0.0051 (10) |
C14 | 0.0415 (11) | 0.0343 (10) | 0.0470 (11) | 0.0006 (8) | 0.0167 (9) | 0.0055 (8) |
C15 | 0.0463 (13) | 0.0466 (12) | 0.0610 (14) | 0.0015 (10) | 0.0110 (11) | 0.0021 (10) |
C16 | 0.0491 (14) | 0.0554 (14) | 0.0924 (19) | 0.0101 (12) | 0.0153 (13) | 0.0088 (14) |
C17 | 0.0692 (18) | 0.0519 (14) | 0.104 (2) | 0.0148 (13) | 0.0430 (17) | 0.0012 (14) |
C18 | 0.0850 (19) | 0.0473 (13) | 0.0684 (15) | −0.0002 (13) | 0.0385 (15) | −0.0042 (11) |
C19 | 0.0556 (14) | 0.0371 (10) | 0.0477 (12) | −0.0034 (10) | 0.0219 (10) | 0.0032 (9) |
Geometric parameters (Å, º) top
Cd1—N1 | 2.2438 (16) | C6—C7 | 1.406 (3) |
Cd1—O1 | 2.3247 (15) | C6—H6 | 0.9300 |
Cd1—O2 | 2.4246 (14) | C7—C8 | 1.415 (3) |
O1—C1 | 1.246 (2) | C7—C12 | 1.425 (3) |
O2—C1 | 1.257 (2) | C8—C9 | 1.352 (4) |
Cd1—N1i | 2.2438 (16) | C8—H8 | 0.9300 |
Cd1—O1i | 2.3247 (15) | C9—C10 | 1.387 (4) |
Cd1—O2i | 2.4246 (14) | C9—H9A | 0.9300 |
N1—C13 | 1.310 (3) | C10—C11 | 1.361 (3) |
N1—C14 | 1.392 (2) | C10—H10 | 0.9300 |
N2—C13 | 1.333 (3) | C11—C12 | 1.415 (3) |
N2—C19 | 1.371 (3) | C11—H11 | 0.9300 |
N2—H2 | 0.8600 | C13—H13 | 0.9300 |
O1W—H1W1 | 0.85 (4) | C14—C15 | 1.388 (3) |
C1—C2 | 1.517 (3) | C14—C19 | 1.396 (3) |
C2—C3 | 1.507 (3) | C15—C16 | 1.375 (3) |
C2—H2A | 0.9700 | C15—H15 | 0.9300 |
C2—H2B | 0.9700 | C16—C17 | 1.390 (4) |
C3—C4 | 1.365 (3) | C16—H16 | 0.9300 |
C3—C12 | 1.424 (3) | C17—C18 | 1.369 (4) |
C4—C5 | 1.400 (3) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.387 (3) |
C5—C6 | 1.354 (4) | C18—H18 | 0.9300 |
C5—H5A | 0.9300 | | |
| | | |
N1—Cd1—N1i | 103.01 (8) | C4—C3—C2 | 120.8 (2) |
N1—Cd1—O1 | 90.23 (6) | C4—C3—C12 | 118.7 (2) |
N1i—Cd1—O1 | 103.21 (6) | C4—C5—H5A | 120.2 |
N1—Cd1—O2 | 143.05 (5) | C5—C4—H4 | 118.9 |
N1i—Cd1—O2 | 96.93 (5) | C5—C6—C7 | 121.3 (2) |
O1i—Cd1—O1 | 158.47 (8) | C5—C6—H6 | 119.4 |
O1i—Cd1—O2 | 107.54 (5) | C6—C5—C4 | 119.6 (2) |
O1—Cd1—O2 | 54.74 (5) | C6—C5—H5A | 120.2 |
O2i—Cd1—O2 | 84.73 (7) | C6—C7—C8 | 122.7 (2) |
N1—Cd1—O1i | 103.21 (6) | C6—C7—C12 | 118.8 (2) |
N1i—Cd1—O1i | 90.23 (6) | C7—C6—H6 | 119.4 |
N1—Cd1—O2i | 96.93 (5) | C7—C8—H8 | 119.3 |
N1i—Cd1—O2i | 143.05 (5) | C8—C7—C12 | 118.4 (2) |
N1—Cd1—C1i | 101.03 (6) | C8—C9—C10 | 120.6 (2) |
N1i—Cd1—C1i | 116.80 (6) | C8—C9—H9A | 119.7 |
N1—Cd1—C1 | 116.80 (6) | C9—C8—C7 | 121.4 (2) |
N1i—Cd1—C1 | 101.03 (6) | C9—C8—H8 | 119.3 |
N1—C13—N2 | 113.22 (19) | C9—C10—H10 | 120.0 |
N1—C13—H13 | 123.4 | C10—C9—H9A | 119.7 |
N1—C14—C19 | 108.51 (18) | C10—C11—C12 | 121.8 (2) |
N2—C13—H13 | 123.4 | C10—C11—H11 | 119.1 |
N2—C19—C18 | 133.0 (2) | C11—C10—C9 | 120.1 (2) |
N2—C19—C14 | 105.61 (18) | C11—C10—H10 | 120.0 |
O1i—Cd1—O2i | 54.74 (5) | C11—C12—C3 | 123.04 (19) |
O1—Cd1—O2i | 107.54 (5) | C11—C12—C7 | 117.7 (2) |
O1i—Cd1—C1i | 27.19 (6) | C12—C3—C2 | 120.42 (18) |
O1—Cd1—C1i | 134.17 (6) | C12—C11—H11 | 119.1 |
O1i—Cd1—C1 | 134.17 (6) | C13—N1—C14 | 105.22 (17) |
O1—Cd1—C1 | 27.19 (6) | C13—N1—Cd1 | 125.34 (14) |
O2i—Cd1—C1i | 27.55 (5) | C13—N2—C19 | 107.44 (17) |
O2—Cd1—C1i | 97.15 (5) | C13—N2—H2 | 126.3 |
O2i—Cd1—C1 | 97.15 (5) | C14—N1—Cd1 | 129.20 (13) |
O2—Cd1—C1 | 27.55 (5) | C14—C15—H15 | 121.4 |
C1i—Cd1—C1 | 117.90 (9) | C15—C14—N1 | 130.56 (19) |
C1—O1—Cd1 | 94.31 (12) | C15—C14—C19 | 120.93 (19) |
C1—O2—Cd1 | 89.36 (12) | C15—C16—C17 | 121.6 (2) |
O1—C1—Cd1 | 58.50 (11) | C15—C16—H16 | 119.2 |
O1—C1—O2 | 121.58 (19) | C16—C15—C14 | 117.2 (2) |
O1—C1—C2 | 118.48 (19) | C16—C15—H15 | 121.4 |
O2—C1—Cd1 | 63.09 (10) | C16—C17—H17 | 119.1 |
O2—C1—C2 | 119.91 (19) | C17—C16—H16 | 119.2 |
C1—C2—H2A | 108.4 | C17—C18—C19 | 117.1 (2) |
C1—C2—H2B | 108.4 | C17—C18—H18 | 121.5 |
C2—C1—Cd1 | 176.95 (16) | C18—C17—C16 | 121.8 (2) |
C3—C2—C1 | 115.53 (17) | C18—C17—H17 | 119.1 |
C3—C2—H2A | 108.4 | C18—C19—C14 | 121.4 (2) |
C3—C2—H2B | 108.4 | C19—N2—H2 | 126.3 |
C3—C4—C5 | 122.3 (2) | C19—C18—H18 | 121.5 |
C3—C4—H4 | 118.9 | H2A—C2—H2B | 107.5 |
C3—C12—C7 | 119.25 (19) | | |
| | | |
Cd1—N1—C13—N2 | 175.20 (12) | C1i—Cd1—N1—C14 | 44.43 (17) |
Cd1—N1—C14—C15 | 5.6 (3) | C1—Cd1—N1—C14 | 173.66 (15) |
Cd1—N1—C14—C19 | −174.53 (12) | C1i—Cd1—O1—C1 | −62.40 (18) |
Cd1—O1—C1—O2 | 1.3 (2) | C1i—Cd1—O2—C1 | 141.19 (10) |
Cd1—O1—C1—C2 | 179.51 (16) | C1i—Cd1—C1—O1 | 134.01 (14) |
Cd1—O2—C1—O1 | −1.3 (2) | C1i—Cd1—C1—O2 | −44.72 (10) |
Cd1—O2—C1—C2 | −179.42 (17) | C1—C2—C3—C4 | 112.2 (2) |
N1i—Cd1—N1—C13 | 109.73 (17) | C1—C2—C3—C12 | −68.5 (3) |
N1i—Cd1—N1—C14 | −76.67 (15) | C2—C3—C4—C5 | 178.7 (2) |
N1—Cd1—O1—C1 | −168.11 (13) | C2—C3—C12—C7 | −179.34 (18) |
N1i—Cd1—O1—C1 | 88.47 (13) | C2—C3—C12—C11 | 0.7 (3) |
N1—Cd1—O2—C1 | 22.02 (16) | C3—C4—C5—C6 | 0.9 (4) |
N1i—Cd1—O2—C1 | −100.58 (12) | C4—C3—C12—C7 | 0.0 (3) |
N1—Cd1—C1—O1 | 13.35 (15) | C4—C3—C12—C11 | −180.0 (2) |
N1i—Cd1—C1—O1 | −97.47 (13) | C4—C5—C6—C7 | −0.5 (4) |
N1—Cd1—C1—O2 | −165.38 (11) | C5—C6—C7—C8 | 179.1 (2) |
N1i—Cd1—C1—O2 | 83.81 (12) | C5—C6—C7—C12 | −0.1 (3) |
N1—C14—C15—C16 | −179.7 (2) | C6—C7—C8—C9 | −179.4 (2) |
N1—C14—C19—N2 | −0.4 (2) | C6—C7—C12—C3 | 0.4 (3) |
N1—C14—C19—C18 | 179.84 (18) | C6—C7—C12—C11 | −179.7 (2) |
O1i—Cd1—N1—C13 | −156.92 (16) | C7—C8—C9—C10 | −0.5 (4) |
O1—Cd1—N1—C13 | 6.11 (16) | C8—C7—C12—C3 | −178.93 (19) |
O1i—Cd1—N1—C14 | 16.69 (17) | C8—C7—C12—C11 | 1.0 (3) |
O1—Cd1—N1—C14 | 179.72 (16) | C8—C9—C10—C11 | 0.3 (4) |
O1i—Cd1—O1—C1 | −38.85 (12) | C9—C10—C11—C12 | 0.6 (4) |
O1i—Cd1—O2—C1 | 166.97 (11) | C10—C11—C12—C3 | 178.7 (2) |
O1—Cd1—O2—C1 | 0.71 (11) | C10—C11—C12—C7 | −1.2 (3) |
O1i—Cd1—C1—O1 | 161.28 (9) | C12—C3—C4—C5 | −0.6 (3) |
O1i—Cd1—C1—O2 | −17.44 (15) | C12—C7—C8—C9 | −0.2 (3) |
O1—Cd1—C1—O2 | −178.7 (2) | C13—N1—C14—C15 | −179.8 (2) |
O1—C1—C2—C3 | 158.05 (19) | C13—N1—C14—C19 | 0.1 (2) |
O2i—Cd1—N1—C13 | −101.59 (16) | C13—N2—C19—C18 | −179.7 (2) |
O2—Cd1—N1—C13 | −11.1 (2) | C13—N2—C19—C14 | 0.6 (2) |
O2i—Cd1—N1—C14 | 72.02 (16) | C14—N1—C13—N2 | 0.3 (2) |
O2—Cd1—N1—C14 | 162.46 (13) | C14—C15—C16—C17 | −0.2 (4) |
O2i—Cd1—O1—C1 | −70.76 (13) | C15—C14—C19—N2 | 179.43 (18) |
O2—Cd1—O1—C1 | −0.72 (11) | C15—C14—C19—C18 | −0.3 (3) |
O2i—Cd1—O2—C1 | 116.55 (12) | C15—C16—C17—C18 | −0.3 (4) |
O2—Cd1—C1—O1 | 178.7 (2) | C16—C17—C18—C19 | 0.5 (4) |
O2i—Cd1—C1—O1 | 114.86 (13) | C17—C18—C19—N2 | −179.8 (2) |
O2i—Cd1—C1—O2 | −63.86 (13) | C17—C18—C19—C14 | −0.2 (3) |
O2—C1—C2—C3 | −23.8 (3) | C19—N2—C13—N1 | −0.6 (2) |
C1i—Cd1—N1—C13 | −129.18 (16) | C19—C14—C15—C16 | 0.5 (3) |
C1—Cd1—N1—C13 | 0.05 (18) | | |
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···O2ii | 0.86 | 1.99 | 2.793 (2) | 154 |
O1W—H1W1···O2i | 0.85 (4) | 2.25 (2) | 2.998 (3) | 147 (2) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+1, z−1/2. |