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The CdII ion of the title mononuclear complex, [Cd(C12H9O2)2(C7H6N2)2]·H2O, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005363/lh2286sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005363/lh2286Isup2.hkl
Contains datablock I

CCDC reference: 640408

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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

Computing details top

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)(1H-benzimidazole)]cadmium(II) monohydrate top
Crystal data top
[Cd(C12H9O2)2(C7H6N2)2]·H2OF(000) = 1504
Mr = 737.08Dx = 1.499 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 12987 reflections
a = 11.8418 (2) Åθ = 2.0–25.1°
b = 20.0552 (4) ŵ = 0.72 mm1
c = 14.3436 (4) ÅT = 273 K
β = 106.571 (1)°Prism, colorless
V = 3264.98 (12) Å30.32 × 0.26 × 0.18 mm
Z = 4
Data collection top
Bruker APEX-2
diffractometer
2873 independent reflections
Radiation source: fine-focus sealed tube2635 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 10 pixels mm-1θmax = 25.1°, θmin = 2.0°
ω scansh = 1413
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2323
Tmin = 0.800, Tmax = 0.871l = 1617
13266 measured reflections
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H 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 parametersΔρmax = 0.32 e Å3
2 restraintsΔρmin = 0.18 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.50000.520475 (10)0.25000.04045 (9)
N10.51505 (14)0.45084 (8)0.13169 (12)0.0424 (4)
N20.46851 (16)0.40116 (8)0.01153 (12)0.0499 (4)
O1W0.50000.73516 (16)0.25000.1530 (19)
O10.30474 (13)0.54213 (8)0.16558 (12)0.0567 (4)
O20.38129 (12)0.60980 (7)0.28649 (10)0.0484 (4)
C10.29575 (17)0.59040 (10)0.21769 (14)0.0422 (5)
C20.17927 (18)0.62734 (12)0.19468 (16)0.0514 (5)
C30.15771 (16)0.66650 (10)0.27766 (15)0.0451 (5)
C40.1541 (2)0.73452 (12)0.27532 (19)0.0589 (6)
C50.1320 (2)0.77234 (12)0.3503 (2)0.0660 (7)
C60.1148 (2)0.74113 (13)0.4289 (2)0.0658 (7)
C70.11791 (18)0.67123 (12)0.43656 (16)0.0520 (5)
C80.1019 (2)0.63708 (15)0.51821 (18)0.0655 (7)
C90.1063 (2)0.56980 (16)0.5240 (2)0.0726 (8)
C100.1259 (2)0.53211 (13)0.4490 (2)0.0648 (7)
C110.14142 (18)0.56275 (11)0.36894 (17)0.0516 (5)
C120.13935 (16)0.63300 (10)0.35963 (15)0.0420 (5)
C130.43384 (19)0.44139 (10)0.04902 (15)0.0467 (5)
C140.61163 (17)0.41383 (9)0.12452 (14)0.0401 (4)
C150.72194 (19)0.40516 (11)0.19043 (17)0.0522 (5)
C160.8005 (2)0.36522 (12)0.1621 (2)0.0666 (7)
C170.7711 (3)0.33456 (12)0.0714 (2)0.0713 (7)
C180.6623 (3)0.34229 (11)0.00601 (19)0.0635 (7)
C190.5824 (2)0.38263 (9)0.03375 (15)0.0453 (5)
H1W10.543 (4)0.7115 (9)0.225 (4)0.230*
H20.42700.38900.06850.060*
H2A0.17520.65770.14120.062*
H2B0.11610.59520.17260.062*
H40.16680.75650.22210.071*
H5A0.12910.81860.34610.079*
H60.10070.76640.47870.079*
H80.08800.66150.56900.079*
H9A0.09610.54860.57870.087*
H100.12830.48580.45350.078*
H110.15380.53680.31900.062*
H130.35950.46080.03410.056*
H150.74180.42550.25120.063*
H160.87520.35850.20460.080*
H170.82680.30810.05470.086*
H180.64280.32140.05440.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.03270 (13)0.04385 (13)0.04581 (14)0.0000.01281 (9)0.000
N10.0398 (10)0.0435 (9)0.0437 (9)0.0011 (8)0.0116 (8)0.0003 (8)
N20.0570 (12)0.0478 (10)0.0412 (10)0.0057 (9)0.0082 (9)0.0003 (8)
O1W0.106 (3)0.063 (2)0.264 (6)0.0000.011 (3)0.000
O10.0438 (9)0.0623 (9)0.0592 (9)0.0081 (7)0.0070 (7)0.0106 (8)
O20.0296 (7)0.0645 (9)0.0486 (8)0.0037 (7)0.0068 (7)0.0031 (7)
C10.0323 (11)0.0517 (12)0.0444 (11)0.0021 (9)0.0136 (9)0.0067 (9)
C20.0348 (11)0.0677 (14)0.0487 (12)0.0076 (10)0.0072 (9)0.0016 (10)
C30.0246 (10)0.0493 (12)0.0586 (13)0.0044 (9)0.0070 (9)0.0010 (10)
C40.0443 (13)0.0539 (13)0.0753 (16)0.0016 (11)0.0121 (12)0.0127 (12)
C50.0565 (15)0.0439 (13)0.0896 (19)0.0022 (11)0.0079 (14)0.0099 (13)
C60.0519 (14)0.0638 (16)0.0763 (17)0.0038 (12)0.0097 (13)0.0254 (14)
C70.0324 (11)0.0636 (14)0.0564 (13)0.0016 (10)0.0067 (10)0.0078 (11)
C80.0406 (13)0.101 (2)0.0539 (14)0.0058 (14)0.0120 (11)0.0085 (14)
C90.0435 (14)0.101 (2)0.0703 (17)0.0136 (15)0.0108 (12)0.0233 (16)
C100.0425 (14)0.0629 (15)0.0850 (19)0.0055 (11)0.0118 (13)0.0156 (14)
C110.0343 (11)0.0509 (12)0.0676 (14)0.0013 (10)0.0114 (10)0.0000 (11)
C120.0239 (10)0.0476 (11)0.0524 (12)0.0010 (8)0.0074 (9)0.0034 (9)
C130.0434 (12)0.0461 (12)0.0494 (12)0.0007 (10)0.0114 (10)0.0051 (10)
C140.0415 (11)0.0343 (10)0.0470 (11)0.0006 (8)0.0167 (9)0.0055 (8)
C150.0463 (13)0.0466 (12)0.0610 (14)0.0015 (10)0.0110 (11)0.0021 (10)
C160.0491 (14)0.0554 (14)0.0924 (19)0.0101 (12)0.0153 (13)0.0088 (14)
C170.0692 (18)0.0519 (14)0.104 (2)0.0148 (13)0.0430 (17)0.0012 (14)
C180.0850 (19)0.0473 (13)0.0684 (15)0.0002 (13)0.0385 (15)0.0042 (11)
C190.0556 (14)0.0371 (10)0.0477 (12)0.0034 (10)0.0219 (10)0.0032 (9)
Geometric parameters (Å, º) top
Cd1—N12.2438 (16)C6—C71.406 (3)
Cd1—O12.3247 (15)C6—H60.9300
Cd1—O22.4246 (14)C7—C81.415 (3)
O1—C11.246 (2)C7—C121.425 (3)
O2—C11.257 (2)C8—C91.352 (4)
Cd1—N1i2.2438 (16)C8—H80.9300
Cd1—O1i2.3247 (15)C9—C101.387 (4)
Cd1—O2i2.4246 (14)C9—H9A0.9300
N1—C131.310 (3)C10—C111.361 (3)
N1—C141.392 (2)C10—H100.9300
N2—C131.333 (3)C11—C121.415 (3)
N2—C191.371 (3)C11—H110.9300
N2—H20.8600C13—H130.9300
O1W—H1W10.85 (4)C14—C151.388 (3)
C1—C21.517 (3)C14—C191.396 (3)
C2—C31.507 (3)C15—C161.375 (3)
C2—H2A0.9700C15—H150.9300
C2—H2B0.9700C16—C171.390 (4)
C3—C41.365 (3)C16—H160.9300
C3—C121.424 (3)C17—C181.369 (4)
C4—C51.400 (3)C17—H170.9300
C4—H40.9300C18—C191.387 (3)
C5—C61.354 (4)C18—H180.9300
C5—H5A0.9300
N1—Cd1—N1i103.01 (8)C4—C3—C2120.8 (2)
N1—Cd1—O190.23 (6)C4—C3—C12118.7 (2)
N1i—Cd1—O1103.21 (6)C4—C5—H5A120.2
N1—Cd1—O2143.05 (5)C5—C4—H4118.9
N1i—Cd1—O296.93 (5)C5—C6—C7121.3 (2)
O1i—Cd1—O1158.47 (8)C5—C6—H6119.4
O1i—Cd1—O2107.54 (5)C6—C5—C4119.6 (2)
O1—Cd1—O254.74 (5)C6—C5—H5A120.2
O2i—Cd1—O284.73 (7)C6—C7—C8122.7 (2)
N1—Cd1—O1i103.21 (6)C6—C7—C12118.8 (2)
N1i—Cd1—O1i90.23 (6)C7—C6—H6119.4
N1—Cd1—O2i96.93 (5)C7—C8—H8119.3
N1i—Cd1—O2i143.05 (5)C8—C7—C12118.4 (2)
N1—Cd1—C1i101.03 (6)C8—C9—C10120.6 (2)
N1i—Cd1—C1i116.80 (6)C8—C9—H9A119.7
N1—Cd1—C1116.80 (6)C9—C8—C7121.4 (2)
N1i—Cd1—C1101.03 (6)C9—C8—H8119.3
N1—C13—N2113.22 (19)C9—C10—H10120.0
N1—C13—H13123.4C10—C9—H9A119.7
N1—C14—C19108.51 (18)C10—C11—C12121.8 (2)
N2—C13—H13123.4C10—C11—H11119.1
N2—C19—C18133.0 (2)C11—C10—C9120.1 (2)
N2—C19—C14105.61 (18)C11—C10—H10120.0
O1i—Cd1—O2i54.74 (5)C11—C12—C3123.04 (19)
O1—Cd1—O2i107.54 (5)C11—C12—C7117.7 (2)
O1i—Cd1—C1i27.19 (6)C12—C3—C2120.42 (18)
O1—Cd1—C1i134.17 (6)C12—C11—H11119.1
O1i—Cd1—C1134.17 (6)C13—N1—C14105.22 (17)
O1—Cd1—C127.19 (6)C13—N1—Cd1125.34 (14)
O2i—Cd1—C1i27.55 (5)C13—N2—C19107.44 (17)
O2—Cd1—C1i97.15 (5)C13—N2—H2126.3
O2i—Cd1—C197.15 (5)C14—N1—Cd1129.20 (13)
O2—Cd1—C127.55 (5)C14—C15—H15121.4
C1i—Cd1—C1117.90 (9)C15—C14—N1130.56 (19)
C1—O1—Cd194.31 (12)C15—C14—C19120.93 (19)
C1—O2—Cd189.36 (12)C15—C16—C17121.6 (2)
O1—C1—Cd158.50 (11)C15—C16—H16119.2
O1—C1—O2121.58 (19)C16—C15—C14117.2 (2)
O1—C1—C2118.48 (19)C16—C15—H15121.4
O2—C1—Cd163.09 (10)C16—C17—H17119.1
O2—C1—C2119.91 (19)C17—C16—H16119.2
C1—C2—H2A108.4C17—C18—C19117.1 (2)
C1—C2—H2B108.4C17—C18—H18121.5
C2—C1—Cd1176.95 (16)C18—C17—C16121.8 (2)
C3—C2—C1115.53 (17)C18—C17—H17119.1
C3—C2—H2A108.4C18—C19—C14121.4 (2)
C3—C2—H2B108.4C19—N2—H2126.3
C3—C4—C5122.3 (2)C19—C18—H18121.5
C3—C4—H4118.9H2A—C2—H2B107.5
C3—C12—C7119.25 (19)
Cd1—N1—C13—N2175.20 (12)C1i—Cd1—N1—C1444.43 (17)
Cd1—N1—C14—C155.6 (3)C1—Cd1—N1—C14173.66 (15)
Cd1—N1—C14—C19174.53 (12)C1i—Cd1—O1—C162.40 (18)
Cd1—O1—C1—O21.3 (2)C1i—Cd1—O2—C1141.19 (10)
Cd1—O1—C1—C2179.51 (16)C1i—Cd1—C1—O1134.01 (14)
Cd1—O2—C1—O11.3 (2)C1i—Cd1—C1—O244.72 (10)
Cd1—O2—C1—C2179.42 (17)C1—C2—C3—C4112.2 (2)
N1i—Cd1—N1—C13109.73 (17)C1—C2—C3—C1268.5 (3)
N1i—Cd1—N1—C1476.67 (15)C2—C3—C4—C5178.7 (2)
N1—Cd1—O1—C1168.11 (13)C2—C3—C12—C7179.34 (18)
N1i—Cd1—O1—C188.47 (13)C2—C3—C12—C110.7 (3)
N1—Cd1—O2—C122.02 (16)C3—C4—C5—C60.9 (4)
N1i—Cd1—O2—C1100.58 (12)C4—C3—C12—C70.0 (3)
N1—Cd1—C1—O113.35 (15)C4—C3—C12—C11180.0 (2)
N1i—Cd1—C1—O197.47 (13)C4—C5—C6—C70.5 (4)
N1—Cd1—C1—O2165.38 (11)C5—C6—C7—C8179.1 (2)
N1i—Cd1—C1—O283.81 (12)C5—C6—C7—C120.1 (3)
N1—C14—C15—C16179.7 (2)C6—C7—C8—C9179.4 (2)
N1—C14—C19—N20.4 (2)C6—C7—C12—C30.4 (3)
N1—C14—C19—C18179.84 (18)C6—C7—C12—C11179.7 (2)
O1i—Cd1—N1—C13156.92 (16)C7—C8—C9—C100.5 (4)
O1—Cd1—N1—C136.11 (16)C8—C7—C12—C3178.93 (19)
O1i—Cd1—N1—C1416.69 (17)C8—C7—C12—C111.0 (3)
O1—Cd1—N1—C14179.72 (16)C8—C9—C10—C110.3 (4)
O1i—Cd1—O1—C138.85 (12)C9—C10—C11—C120.6 (4)
O1i—Cd1—O2—C1166.97 (11)C10—C11—C12—C3178.7 (2)
O1—Cd1—O2—C10.71 (11)C10—C11—C12—C71.2 (3)
O1i—Cd1—C1—O1161.28 (9)C12—C3—C4—C50.6 (3)
O1i—Cd1—C1—O217.44 (15)C12—C7—C8—C90.2 (3)
O1—Cd1—C1—O2178.7 (2)C13—N1—C14—C15179.8 (2)
O1—C1—C2—C3158.05 (19)C13—N1—C14—C190.1 (2)
O2i—Cd1—N1—C13101.59 (16)C13—N2—C19—C18179.7 (2)
O2—Cd1—N1—C1311.1 (2)C13—N2—C19—C140.6 (2)
O2i—Cd1—N1—C1472.02 (16)C14—N1—C13—N20.3 (2)
O2—Cd1—N1—C14162.46 (13)C14—C15—C16—C170.2 (4)
O2i—Cd1—O1—C170.76 (13)C15—C14—C19—N2179.43 (18)
O2—Cd1—O1—C10.72 (11)C15—C14—C19—C180.3 (3)
O2i—Cd1—O2—C1116.55 (12)C15—C16—C17—C180.3 (4)
O2—Cd1—C1—O1178.7 (2)C16—C17—C18—C190.5 (4)
O2i—Cd1—C1—O1114.86 (13)C17—C18—C19—N2179.8 (2)
O2i—Cd1—C1—O263.86 (13)C17—C18—C19—C140.2 (3)
O2—C1—C2—C323.8 (3)C19—N2—C13—N10.6 (2)
C1i—Cd1—N1—C13129.18 (16)C19—C14—C15—C160.5 (3)
C1—Cd1—N1—C130.05 (18)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2ii0.861.992.793 (2)154
O1W—H1W1···O2i0.85 (4)2.25 (2)2.998 (3)147 (2)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x, y+1, z1/2.
 

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