Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023604/bt2365sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023604/bt2365Isup2.hkl |
CCDC reference: 650703
Zinc diacetate dihydrate (0.11 g, 0.5 mmol) was added to a 1:1 aqueous-ethanol solution (20 ml) of 4-formylbenzoic acid (0.15 g, 1 mmol) and benzimidazole (0.07 g, 1 mmol). Sodium hydroxide was added to a pH value of about 5. The filtered solution was set aside for the formation of colorless prismatic crystals. CH&N analysis. Calculated for C30H24N4O7Zn: C 58.31, H 3.91, N 9.07%. Found: C 58.28, H 3.93, N 9.04%.
One of the two formylbenzoate anions is disordered over two positions; the occupancy factors refined to 0.535 (5):0.465 (5). For both components, the phenylene ring was refined as a rigid hexagon of 1.39Å sides. The C–C single-bond length was restrained to 1.50±0.01Å and the C=O double-bond distance to 1.25±0.01 Å. The Caliphatic···Cortho distances were restrained to 2.50±0.01 Å and the entire anion was restrained to be planar. As the C8 atom is less than 0.2 Å from C8', the temperature factors were restrained to be identical; those of the O3 and O3' were similarly treated for the same reason. Additionally, the disordered atoms were restrained to be nearly isotropic. A consideration of the hydrogen bonding distances led to pairing the O1w' water molecule with the primed anion.
The carbon- and nitrogen bound H atoms were generated geometrically (C–H 0.93, N–H 0.86 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The water H atoms could were placed in chemically sensible positions on the basis of hydrogen bonding interactions but they were not refined.
Bis(4-formylbenzoato)zinc, which exists as a tetrahedral diaqua compound (Deng et al., 2006a), form a five-coordinate aqua complex with phenathroline (Deng et al., 2006b). The title compound is a 1:2 adduct of Bis(4-formylbenzoato)zinc with benzimidazole, crystallizing with a molecule of water (I). The metal center shows tetrahedral coordination (Fig. 1). Adjacent molecules are linked by hydrogen bonds.
For the diaqua complex, see Deng et al., 2006a, and for the aqua phenanthroline adduct, see Deng et al., 2006b.
Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).
[Zn(C8H5O3)2(C7H6N2)2].H2O | F(000) = 2544 |
Mr = 617.90 | Dx = 1.465 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 13980 reflections |
a = 13.7968 (8) Å | θ = 3.1–27.5° |
b = 17.0524 (8) Å | µ = 0.93 mm−1 |
c = 23.848 (1) Å | T = 295 K |
β = 92.954 (1)° | Prism, colourless |
V = 5603.1 (5) Å3 | 0.35 × 0.26 × 0.19 mm |
Z = 8 |
Rigaku RAXIS-RAPID IP diffractometer | 6393 independent reflections |
Radiation source: fine-focus sealed tube | 3298 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
ω scan | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −17→17 |
Tmin = 0.558, Tmax = 0.843 | k = −21→22 |
27096 measured reflections | l = −30→30 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.194 | w = 1/[σ2(Fo2) + (0.0884P)2 + 4.8786P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
6393 reflections | Δρmax = 0.70 e Å−3 |
453 parameters | Δρmin = −0.67 e Å−3 |
178 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0008 (2) |
[Zn(C8H5O3)2(C7H6N2)2].H2O | V = 5603.1 (5) Å3 |
Mr = 617.90 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.7968 (8) Å | µ = 0.93 mm−1 |
b = 17.0524 (8) Å | T = 295 K |
c = 23.848 (1) Å | 0.35 × 0.26 × 0.19 mm |
β = 92.954 (1)° |
Rigaku RAXIS-RAPID IP diffractometer | 6393 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3298 reflections with I > 2σ(I) |
Tmin = 0.558, Tmax = 0.843 | Rint = 0.068 |
27096 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 178 restraints |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.70 e Å−3 |
6393 reflections | Δρmin = −0.67 e Å−3 |
453 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.28971 (4) | 0.59229 (3) | 0.38356 (2) | 0.0525 (2) | |
N1 | 0.2248 (3) | 0.4871 (2) | 0.36616 (14) | 0.0554 (9) | |
N2 | 0.1303 (3) | 0.4014 (2) | 0.32177 (19) | 0.0726 (12) | |
H2n | 0.0868 | 0.3830 | 0.2982 | 0.087* | |
N3 | 0.2451 (3) | 0.6254 (2) | 0.45870 (14) | 0.0522 (9) | |
N4 | 0.2390 (3) | 0.6728 (2) | 0.54477 (15) | 0.0606 (10) | |
H4n | 0.2587 | 0.6909 | 0.5770 | 0.073* | |
O4 | 0.2136 (3) | 0.64849 (19) | 0.32459 (13) | 0.0658 (9) | |
O5 | 0.2842 (3) | 0.7626 (2) | 0.34589 (14) | 0.0768 (10) | |
O6 | −0.0635 (3) | 0.8200 (3) | 0.10574 (17) | 0.1046 (15) | |
O1 | 0.4180 (6) | 0.5925 (4) | 0.3560 (4) | 0.079 (2) | 0.535 (5) |
O2 | 0.4492 (6) | 0.5579 (4) | 0.4422 (4) | 0.103 (3) | 0.535 (5) |
O3 | 0.9173 (18) | 0.5162 (7) | 0.3088 (8) | 0.098 (2) | 0.535 (5) |
O1w | 0.4534 (8) | 0.7360 (6) | 0.2980 (5) | 0.141 (4) | 0.535 (5) |
H1w1 | 0.4569 | 0.6904 | 0.3115 | 0.169* | 0.535 (5) |
H1w2 | 0.4005 | 0.7568 | 0.3089 | 0.169* | 0.535 (5) |
C1 | 0.4754 (5) | 0.5692 (3) | 0.3940 (4) | 0.072 (4) | 0.535 (5) |
C2 | 0.5795 (4) | 0.5542 (3) | 0.3815 (3) | 0.061 (3) | 0.535 (5) |
C7 | 0.6133 (5) | 0.5658 (3) | 0.3283 (2) | 0.054 (3) | 0.535 (5) |
H7 | 0.5712 | 0.5833 | 0.2992 | 0.064* | 0.535 (5) |
C6 | 0.7101 (5) | 0.5513 (4) | 0.3184 (3) | 0.051 (2) | 0.535 (5) |
H6 | 0.7327 | 0.5590 | 0.2827 | 0.061* | 0.535 (5) |
C5 | 0.7731 (4) | 0.5251 (5) | 0.3618 (4) | 0.059 (4) | 0.535 (5) |
C4 | 0.7393 (5) | 0.5135 (5) | 0.4150 (3) | 0.065 (3) | 0.535 (5) |
H4 | 0.7814 | 0.4959 | 0.4441 | 0.078* | 0.535 (5) |
C3 | 0.6425 (6) | 0.5280 (4) | 0.4249 (2) | 0.069 (3) | 0.535 (5) |
H3 | 0.6199 | 0.5202 | 0.4606 | 0.083* | 0.535 (5) |
C8 | 0.8764 (6) | 0.5092 (6) | 0.3522 (6) | 0.078 (2) | 0.535 (5) |
H8 | 0.9143 | 0.4918 | 0.3831 | 0.094* | 0.535 (5) |
O1' | 0.4345 (9) | 0.5846 (5) | 0.3997 (5) | 0.090 (3) | 0.465 (5) |
O2' | 0.4298 (7) | 0.6000 (5) | 0.3094 (5) | 0.116 (4) | 0.465 (5) |
O3' | 0.915 (2) | 0.4944 (9) | 0.3035 (9) | 0.098 (2) | 0.465 (3) |
O1w' | 0.4547 (5) | 0.8194 (4) | 0.2757 (3) | 0.061 (2) | 0.465 (5) |
H1w3 | 0.4127 | 0.8226 | 0.3009 | 0.073* | 0.465 (5) |
H1w4 | 0.4651 | 0.7706 | 0.2692 | 0.073* | 0.465 (5) |
C1' | 0.4733 (6) | 0.5834 (4) | 0.3539 (4) | 0.077 (4) | 0.465 (5) |
C2' | 0.5783 (5) | 0.5604 (3) | 0.3534 (4) | 0.074 (4) | 0.465 (5) |
C7' | 0.6228 (6) | 0.5587 (5) | 0.3025 (3) | 0.094 (5) | 0.465 (5) |
H7' | 0.5876 | 0.5717 | 0.2694 | 0.113* | 0.465 (5) |
C6' | 0.7200 (6) | 0.5377 (5) | 0.3009 (4) | 0.067 (4) | 0.465 (5) |
H6' | 0.7498 | 0.5365 | 0.2668 | 0.081* | 0.465 (5) |
C5' | 0.7725 (5) | 0.5183 (6) | 0.3502 (5) | 0.058 (4) | 0.465 (5) |
C4' | 0.7280 (7) | 0.5200 (6) | 0.4011 (4) | 0.072 (4) | 0.465 (5) |
H4' | 0.7632 | 0.5071 | 0.4342 | 0.086* | 0.465 (5) |
C3' | 0.6308 (6) | 0.5411 (5) | 0.4028 (3) | 0.072 (4) | 0.465 (5) |
H3' | 0.6010 | 0.5422 | 0.4368 | 0.087* | 0.465 (5) |
C8' | 0.8763 (7) | 0.4958 (8) | 0.3482 (7) | 0.078 (2) | 0.465 |
H8' | 0.9117 | 0.4828 | 0.3812 | 0.094* | 0.465 (5) |
C9 | 0.2289 (4) | 0.7213 (3) | 0.31636 (18) | 0.0580 (12) | |
C10 | 0.1726 (3) | 0.7564 (3) | 0.26685 (17) | 0.0531 (11) | |
C11 | 0.1190 (4) | 0.7085 (3) | 0.22931 (19) | 0.0687 (14) | |
H11 | 0.1211 | 0.6544 | 0.2338 | 0.082* | |
C12 | 0.0636 (4) | 0.7405 (3) | 0.1862 (2) | 0.0707 (14) | |
H12 | 0.0291 | 0.7081 | 0.1610 | 0.085* | |
C13 | 0.0587 (4) | 0.8214 (3) | 0.17986 (18) | 0.0588 (12) | |
C14 | 0.1134 (4) | 0.8688 (3) | 0.2157 (2) | 0.0605 (12) | |
H14 | 0.1117 | 0.9229 | 0.2107 | 0.073* | |
C15 | 0.1708 (3) | 0.8370 (3) | 0.25929 (18) | 0.0578 (12) | |
H15 | 0.2079 | 0.8695 | 0.2833 | 0.069* | |
C16 | −0.0066 (4) | 0.8548 (4) | 0.1356 (2) | 0.0796 (16) | |
H16 | −0.0032 | 0.9087 | 0.1303 | 0.096* | |
C17 | 0.2429 (3) | 0.4136 (3) | 0.38937 (17) | 0.0514 (11) | |
C18 | 0.3076 (4) | 0.3910 (3) | 0.4323 (2) | 0.0693 (14) | |
H18 | 0.3472 | 0.4272 | 0.4516 | 0.083* | |
C19 | 0.3107 (5) | 0.3118 (4) | 0.4455 (3) | 0.094 (2) | |
H19 | 0.3533 | 0.2945 | 0.4743 | 0.113* | |
C20 | 0.2518 (5) | 0.2577 (4) | 0.4165 (3) | 0.096 (2) | |
H20 | 0.2562 | 0.2050 | 0.4264 | 0.115* | |
C21 | 0.1878 (4) | 0.2798 (3) | 0.3739 (3) | 0.0748 (15) | |
H21 | 0.1486 | 0.2435 | 0.3546 | 0.090* | |
C22 | 0.1838 (4) | 0.3586 (3) | 0.36096 (19) | 0.0569 (11) | |
C23 | 0.1566 (4) | 0.4757 (3) | 0.3263 (2) | 0.0722 (15) | |
H23 | 0.1299 | 0.5156 | 0.3038 | 0.087* | |
C24 | 0.1479 (3) | 0.6321 (3) | 0.47185 (17) | 0.0517 (11) | |
C25 | 0.0638 (4) | 0.6154 (3) | 0.4404 (2) | 0.0715 (14) | |
H25 | 0.0656 | 0.5964 | 0.4039 | 0.086* | |
C26 | −0.0223 (4) | 0.6278 (4) | 0.4648 (2) | 0.0824 (16) | |
H26 | −0.0801 | 0.6174 | 0.4443 | 0.099* | |
C27 | −0.0258 (4) | 0.6556 (4) | 0.5192 (2) | 0.0814 (16) | |
H27 | −0.0858 | 0.6615 | 0.5347 | 0.098* | |
C28 | 0.0567 (4) | 0.6746 (3) | 0.5511 (2) | 0.0720 (15) | |
H28 | 0.0541 | 0.6948 | 0.5872 | 0.086* | |
C29 | 0.1443 (4) | 0.6621 (3) | 0.52625 (17) | 0.0541 (11) | |
C30 | 0.2954 (4) | 0.6502 (2) | 0.50375 (18) | 0.0559 (11) | |
H30 | 0.3628 | 0.6517 | 0.5067 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0559 (4) | 0.0557 (3) | 0.0447 (3) | 0.0063 (2) | −0.0098 (2) | −0.0017 (2) |
N1 | 0.054 (2) | 0.061 (2) | 0.050 (2) | 0.0063 (18) | −0.0054 (17) | −0.0018 (18) |
N2 | 0.072 (3) | 0.069 (3) | 0.073 (3) | −0.005 (2) | −0.024 (2) | −0.014 (2) |
N3 | 0.053 (2) | 0.054 (2) | 0.048 (2) | 0.0027 (17) | −0.0162 (16) | 0.0006 (17) |
N4 | 0.080 (3) | 0.059 (2) | 0.0417 (19) | −0.002 (2) | −0.0088 (19) | −0.0067 (18) |
O4 | 0.077 (2) | 0.061 (2) | 0.0581 (19) | 0.0088 (17) | −0.0127 (16) | 0.0081 (16) |
O5 | 0.095 (3) | 0.079 (2) | 0.0533 (19) | 0.006 (2) | −0.0263 (18) | −0.0135 (18) |
O6 | 0.092 (3) | 0.144 (4) | 0.075 (3) | 0.020 (3) | −0.029 (2) | 0.024 (3) |
O1 | 0.071 (5) | 0.081 (5) | 0.085 (5) | 0.008 (4) | 0.012 (4) | 0.010 (4) |
O2 | 0.102 (6) | 0.109 (5) | 0.102 (6) | 0.021 (4) | 0.035 (5) | 0.014 (5) |
O3 | 0.077 (3) | 0.112 (6) | 0.103 (4) | 0.014 (5) | 0.003 (3) | −0.003 (4) |
O1w | 0.129 (7) | 0.136 (7) | 0.161 (7) | −0.003 (6) | 0.038 (6) | 0.018 (6) |
C1 | 0.090 (8) | 0.053 (5) | 0.073 (7) | 0.003 (5) | 0.015 (6) | −0.004 (5) |
C2 | 0.060 (6) | 0.062 (5) | 0.058 (6) | −0.003 (5) | −0.014 (5) | −0.020 (5) |
C7 | 0.045 (5) | 0.044 (4) | 0.068 (6) | −0.006 (4) | −0.029 (5) | −0.009 (4) |
C6 | 0.058 (6) | 0.047 (5) | 0.045 (5) | −0.002 (4) | −0.007 (4) | −0.014 (4) |
C5 | 0.048 (7) | 0.054 (6) | 0.073 (6) | −0.006 (5) | −0.017 (5) | −0.005 (5) |
C4 | 0.065 (6) | 0.067 (6) | 0.061 (5) | −0.010 (5) | −0.016 (5) | 0.003 (5) |
C3 | 0.073 (7) | 0.071 (6) | 0.063 (6) | 0.002 (5) | −0.002 (5) | −0.002 (5) |
C8 | 0.070 (4) | 0.075 (4) | 0.089 (4) | 0.004 (3) | −0.009 (3) | 0.007 (3) |
O1' | 0.093 (7) | 0.091 (6) | 0.089 (7) | −0.002 (5) | 0.015 (6) | −0.007 (5) |
O2' | 0.078 (6) | 0.163 (8) | 0.104 (7) | 0.030 (5) | −0.014 (5) | −0.027 (6) |
O3' | 0.077 (3) | 0.112 (6) | 0.103 (4) | 0.014 (5) | 0.003 (3) | −0.003 (4) |
O1w' | 0.055 (4) | 0.058 (4) | 0.069 (4) | −0.008 (3) | 0.000 (3) | 0.000 (3) |
C1' | 0.075 (8) | 0.079 (7) | 0.075 (7) | 0.028 (6) | −0.003 (6) | −0.014 (6) |
C2' | 0.065 (7) | 0.069 (7) | 0.088 (9) | 0.011 (6) | 0.000 (7) | −0.006 (6) |
C7' | 0.087 (8) | 0.108 (8) | 0.086 (8) | 0.014 (7) | −0.002 (7) | −0.007 (7) |
C6' | 0.064 (7) | 0.072 (7) | 0.065 (7) | 0.007 (5) | −0.002 (5) | −0.014 (6) |
C5' | 0.052 (8) | 0.058 (7) | 0.063 (6) | −0.003 (6) | −0.011 (5) | −0.001 (6) |
C4' | 0.068 (8) | 0.069 (7) | 0.075 (7) | −0.006 (6) | −0.023 (6) | 0.009 (6) |
C3' | 0.069 (8) | 0.077 (7) | 0.071 (7) | −0.026 (6) | 0.012 (6) | −0.003 (6) |
C8' | 0.070 (4) | 0.075 (4) | 0.089 (4) | 0.004 (3) | −0.009 (3) | 0.007 (3) |
C9 | 0.064 (3) | 0.065 (3) | 0.044 (2) | 0.015 (2) | −0.006 (2) | −0.006 (2) |
C10 | 0.060 (3) | 0.056 (3) | 0.043 (2) | 0.013 (2) | −0.003 (2) | 0.000 (2) |
C11 | 0.091 (4) | 0.056 (3) | 0.056 (3) | 0.013 (3) | −0.023 (3) | −0.005 (2) |
C12 | 0.082 (4) | 0.077 (3) | 0.051 (3) | 0.010 (3) | −0.023 (2) | −0.005 (3) |
C13 | 0.056 (3) | 0.076 (3) | 0.045 (2) | 0.017 (2) | 0.003 (2) | 0.012 (2) |
C14 | 0.058 (3) | 0.063 (3) | 0.061 (3) | 0.009 (2) | 0.004 (2) | 0.014 (2) |
C15 | 0.057 (3) | 0.065 (3) | 0.050 (2) | 0.000 (2) | 0.000 (2) | 0.004 (2) |
C16 | 0.070 (4) | 0.105 (5) | 0.063 (3) | 0.023 (3) | −0.005 (3) | 0.022 (3) |
C17 | 0.055 (3) | 0.058 (3) | 0.042 (2) | 0.012 (2) | 0.0107 (19) | 0.000 (2) |
C18 | 0.075 (4) | 0.076 (3) | 0.057 (3) | 0.003 (3) | −0.001 (3) | 0.008 (3) |
C19 | 0.098 (5) | 0.096 (5) | 0.089 (4) | 0.014 (4) | −0.005 (4) | 0.036 (4) |
C20 | 0.099 (5) | 0.072 (4) | 0.118 (5) | 0.004 (4) | 0.024 (4) | 0.029 (4) |
C21 | 0.075 (4) | 0.064 (3) | 0.087 (4) | −0.007 (3) | 0.023 (3) | −0.005 (3) |
C22 | 0.058 (3) | 0.060 (3) | 0.053 (3) | −0.002 (2) | 0.010 (2) | −0.009 (2) |
C23 | 0.085 (4) | 0.062 (3) | 0.066 (3) | 0.004 (3) | −0.030 (3) | −0.005 (3) |
C24 | 0.053 (3) | 0.054 (3) | 0.047 (2) | 0.003 (2) | −0.009 (2) | 0.001 (2) |
C25 | 0.059 (3) | 0.092 (4) | 0.062 (3) | 0.001 (3) | −0.006 (3) | −0.018 (3) |
C26 | 0.058 (4) | 0.108 (4) | 0.081 (4) | 0.000 (3) | −0.006 (3) | −0.012 (3) |
C27 | 0.072 (4) | 0.105 (5) | 0.068 (3) | 0.003 (3) | 0.015 (3) | −0.003 (3) |
C28 | 0.086 (4) | 0.081 (4) | 0.048 (3) | 0.011 (3) | 0.006 (3) | 0.001 (3) |
C29 | 0.064 (3) | 0.056 (3) | 0.041 (2) | 0.000 (2) | −0.004 (2) | −0.001 (2) |
C30 | 0.067 (3) | 0.050 (2) | 0.050 (2) | −0.002 (2) | −0.014 (2) | 0.002 (2) |
Zn1—O1 | 1.919 (9) | C7'—H7' | 0.9300 |
Zn1—O4 | 1.961 (3) | C6'—C5' | 1.3900 |
Zn1—N3 | 2.006 (4) | C6'—H6' | 0.9300 |
Zn1—O1' | 2.020 (13) | C5'—C4' | 1.3900 |
Zn1—N1 | 2.038 (4) | C5'—C8' | 1.485 (6) |
N1—C23 | 1.316 (6) | C4'—C3' | 1.3900 |
N1—C17 | 1.387 (5) | C4'—H4' | 0.9300 |
N2—C23 | 1.321 (6) | C3'—H3' | 0.9300 |
N2—C22 | 1.372 (6) | C8'—H8' | 0.9300 |
N2—H2n | 0.8600 | C9—C10 | 1.504 (6) |
N3—C30 | 1.318 (5) | C10—C15 | 1.386 (6) |
N3—C24 | 1.397 (6) | C10—C11 | 1.395 (6) |
N4—C30 | 1.338 (6) | C11—C12 | 1.362 (6) |
N4—C29 | 1.370 (6) | C11—H11 | 0.9300 |
N4—H4n | 0.8600 | C12—C13 | 1.389 (7) |
O4—C9 | 1.276 (6) | C12—H12 | 0.9300 |
O5—C9 | 1.232 (6) | C13—C14 | 1.374 (7) |
O6—C16 | 1.190 (7) | C13—C16 | 1.468 (7) |
O1—C1 | 1.237 (8) | C14—C15 | 1.385 (6) |
O2—C1 | 1.239 (8) | C14—H14 | 0.9300 |
O3—C8 | 1.209 (8) | C15—H15 | 0.9300 |
O1w—H1w1 | 0.842 | C16—H16 | 0.9300 |
O1w—H1w2 | 0.864 | C17—C18 | 1.379 (7) |
C1—C2 | 1.504 (6) | C17—C22 | 1.396 (6) |
C2—C7 | 1.3900 | C18—C19 | 1.387 (7) |
C2—C3 | 1.3900 | C18—H18 | 0.9300 |
C7—C6 | 1.3900 | C19—C20 | 1.389 (9) |
C7—H7 | 0.9300 | C19—H19 | 0.9300 |
C6—C5 | 1.3900 | C20—C21 | 1.364 (8) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C5—C4 | 1.3900 | C21—C22 | 1.378 (7) |
C5—C8 | 1.481 (6) | C21—H21 | 0.9300 |
C4—C3 | 1.3900 | C23—H23 | 0.9300 |
C4—H4 | 0.9300 | C24—C25 | 1.379 (6) |
C3—H3 | 0.9300 | C24—C29 | 1.398 (6) |
C8—H8 | 0.9300 | C25—C26 | 1.366 (8) |
O1'—C1' | 1.241 (9) | C25—H25 | 0.9300 |
O2'—C1' | 1.226 (9) | C26—C27 | 1.384 (7) |
O3'—C8' | 1.218 (9) | C26—H26 | 0.9300 |
O1w'—H1w3 | 0.86 | C27—C28 | 1.375 (8) |
O1w'—H1w4 | 0.86 | C27—H27 | 0.9300 |
C1'—C2' | 1.500 (6) | C28—C29 | 1.389 (7) |
C2'—C7' | 1.3900 | C28—H28 | 0.9300 |
C2'—C3' | 1.3900 | C30—H30 | 0.9300 |
C7'—C6' | 1.3900 | ||
O1—Zn1—O4 | 102.9 (3) | C4'—C3'—C2' | 120.0 |
O1—Zn1—N3 | 129.5 (3) | C4'—C3'—H3' | 120.0 |
O4—Zn1—N3 | 108.97 (14) | C2'—C3'—H3' | 120.0 |
O4—Zn1—O1' | 131.0 (3) | O3'—C8'—C5' | 119.9 (18) |
N3—Zn1—O1' | 101.2 (3) | O3'—C8'—H8' | 120.0 |
O1—Zn1—N1 | 109.6 (2) | C5'—C8'—H8' | 120.0 |
O4—Zn1—N1 | 94.03 (14) | O5—C9—O4 | 124.7 (4) |
N3—Zn1—N1 | 106.12 (15) | O5—C9—C10 | 120.1 (4) |
O1'—Zn1—N1 | 113.7 (3) | O4—C9—C10 | 115.2 (4) |
O1—Zn1—C1 | 26.9 (2) | C15—C10—C11 | 119.4 (4) |
O4—Zn1—C1 | 129.3 (2) | C15—C10—C9 | 120.1 (4) |
N3—Zn1—C1 | 107.7 (2) | C11—C10—C9 | 120.4 (4) |
N1—Zn1—C1 | 107.95 (15) | C12—C11—C10 | 120.5 (5) |
C23—N1—C17 | 105.1 (4) | C12—C11—H11 | 119.7 |
C23—N1—Zn1 | 124.6 (3) | C10—C11—H11 | 119.7 |
C17—N1—Zn1 | 130.2 (3) | C11—C12—C13 | 120.1 (5) |
C23—N2—C22 | 108.6 (4) | C11—C12—H12 | 119.9 |
C23—N2—H2n | 125.7 | C13—C12—H12 | 119.9 |
C22—N2—H2n | 125.7 | C14—C13—C12 | 119.7 (4) |
C30—N3—C24 | 105.2 (4) | C14—C13—C16 | 121.1 (5) |
C30—N3—Zn1 | 130.2 (3) | C12—C13—C16 | 119.2 (5) |
C24—N3—Zn1 | 124.5 (3) | C13—C14—C15 | 120.7 (4) |
C30—N4—C29 | 107.9 (4) | C13—C14—H14 | 119.6 |
C30—N4—H4n | 126.1 | C15—C14—H14 | 119.6 |
C29—N4—H4n | 126.1 | C14—C15—C10 | 119.5 (4) |
C9—O4—Zn1 | 119.9 (3) | C14—C15—H15 | 120.3 |
C1—O1—Zn1 | 108.4 (7) | C10—C15—H15 | 120.3 |
H1w1—O1w—H1w2 | 107.3 | O6—C16—C13 | 126.8 (6) |
O1—C1—O2 | 121.5 (9) | O6—C16—H16 | 116.6 |
O1—C1—C2 | 119.5 (7) | C13—C16—H16 | 116.6 |
O2—C1—C2 | 118.9 (7) | C18—C17—N1 | 130.2 (5) |
C7—C2—C3 | 120.0 | C18—C17—C22 | 120.8 (4) |
C7—C2—C1 | 121.6 (4) | N1—C17—C22 | 109.0 (4) |
C3—C2—C1 | 118.4 (4) | C17—C18—C19 | 116.9 (5) |
C2—C7—C6 | 120.0 | C17—C18—H18 | 121.6 |
C2—C7—H7 | 120.0 | C19—C18—H18 | 121.6 |
C6—C7—H7 | 120.0 | C18—C19—C20 | 121.6 (6) |
C7—C6—C5 | 120.0 | C18—C19—H19 | 119.2 |
C7—C6—H6 | 120.0 | C20—C19—H19 | 119.2 |
C5—C6—H6 | 120.0 | C21—C20—C19 | 121.7 (6) |
C6—C5—C4 | 120.0 | C21—C20—H20 | 119.1 |
C6—C5—C8 | 120.9 (5) | C19—C20—H20 | 119.1 |
C4—C5—C8 | 119.1 (5) | C20—C21—C22 | 117.0 (6) |
C3—C4—C5 | 120.0 | C20—C21—H21 | 121.5 |
C3—C4—H4 | 120.0 | C22—C21—H21 | 121.5 |
C5—C4—H4 | 120.0 | N2—C22—C21 | 133.3 (5) |
C4—C3—C2 | 120.0 | N2—C22—C17 | 104.6 (4) |
C4—C3—H3 | 120.0 | C21—C22—C17 | 122.1 (5) |
C2—C3—H3 | 120.0 | N1—C23—N2 | 112.6 (4) |
O3—C8—C5 | 127.5 (16) | N1—C23—H23 | 123.7 |
O3—C8—H8 | 116.2 | N2—C23—H23 | 123.7 |
C5—C8—H8 | 116.2 | C25—C24—N3 | 130.7 (4) |
C1'—O1'—Zn1 | 107.5 (9) | C25—C24—C29 | 120.7 (5) |
H1w3—O1w'—H1w4 | 108.2 | N3—C24—C29 | 108.6 (4) |
O2'—C1'—O1' | 123.0 (11) | C26—C25—C24 | 117.6 (5) |
O2'—C1'—C2' | 118.9 (8) | C26—C25—H25 | 121.2 |
O1'—C1'—C2' | 118.2 (9) | C24—C25—H25 | 121.2 |
C7'—C2'—C3' | 120.0 | C25—C26—C27 | 121.7 (6) |
C7'—C2'—C1' | 118.9 (5) | C25—C26—H26 | 119.2 |
C3'—C2'—C1' | 121.1 (5) | C27—C26—H26 | 119.2 |
C6'—C7'—C2' | 120.0 | C28—C27—C26 | 122.1 (5) |
C6'—C7'—H7' | 120.0 | C28—C27—H27 | 118.9 |
C2'—C7'—H7' | 120.0 | C26—C27—H27 | 118.9 |
C7'—C6'—C5' | 120.0 | C27—C28—C29 | 116.2 (5) |
C7'—C6'—H6' | 120.0 | C27—C28—H28 | 121.9 |
C5'—C6'—H6' | 120.0 | C29—C28—H28 | 121.9 |
C6'—C5'—C4' | 120.0 | N4—C29—C28 | 132.7 (4) |
C6'—C5'—C8' | 119.8 (5) | N4—C29—C24 | 105.6 (4) |
C4'—C5'—C8' | 120.2 (5) | C28—C29—C24 | 121.7 (5) |
C3'—C4'—C5' | 120.0 | N3—C30—N4 | 112.7 (4) |
C3'—C4'—H4' | 120.0 | N3—C30—H30 | 123.6 |
C5'—C4'—H4' | 120.0 | N4—C30—H30 | 123.6 |
O1—Zn1—N1—C23 | −104.9 (5) | O4—C9—C10—C15 | 169.3 (4) |
O4—Zn1—N1—C23 | 0.3 (4) | O5—C9—C10—C11 | 172.2 (5) |
N3—Zn1—N1—C23 | 111.4 (4) | O4—C9—C10—C11 | −8.4 (7) |
O1'—Zn1—N1—C23 | −138.3 (5) | C15—C10—C11—C12 | −1.4 (8) |
C1—Zn1—N1—C23 | −133.3 (4) | C9—C10—C11—C12 | 176.3 (5) |
O1—Zn1—N1—C17 | 71.5 (5) | C10—C11—C12—C13 | −1.1 (8) |
O4—Zn1—N1—C17 | 176.7 (4) | C11—C12—C13—C14 | 2.9 (8) |
N3—Zn1—N1—C17 | −72.2 (4) | C11—C12—C13—C16 | −175.7 (5) |
O1'—Zn1—N1—C17 | 38.1 (5) | C12—C13—C14—C15 | −2.2 (7) |
C1—Zn1—N1—C17 | 43.1 (4) | C16—C13—C14—C15 | 176.5 (4) |
O1—Zn1—N3—C30 | −3.3 (5) | C13—C14—C15—C10 | −0.4 (7) |
O4—Zn1—N3—C30 | −129.4 (4) | C11—C10—C15—C14 | 2.1 (7) |
O1'—Zn1—N3—C30 | 11.5 (5) | C9—C10—C15—C14 | −175.6 (4) |
N1—Zn1—N3—C30 | 130.5 (4) | C14—C13—C16—O6 | −172.6 (6) |
C1—Zn1—N3—C30 | 15.0 (4) | C12—C13—C16—O6 | 6.1 (9) |
O1—Zn1—N3—C24 | 171.5 (4) | C23—N1—C17—C18 | 179.7 (5) |
O4—Zn1—N3—C24 | 45.4 (4) | Zn1—N1—C17—C18 | 2.7 (7) |
O1'—Zn1—N3—C24 | −173.7 (4) | C23—N1—C17—C22 | 1.0 (5) |
N1—Zn1—N3—C24 | −54.8 (3) | Zn1—N1—C17—C22 | −176.0 (3) |
C1—Zn1—N3—C24 | −170.2 (3) | N1—C17—C18—C19 | −178.5 (5) |
O1—Zn1—O4—C9 | −67.1 (4) | C22—C17—C18—C19 | 0.1 (7) |
N3—Zn1—O4—C9 | 73.1 (4) | C17—C18—C19—C20 | 0.3 (9) |
O1'—Zn1—O4—C9 | −51.7 (5) | C18—C19—C20—C21 | −0.2 (10) |
N1—Zn1—O4—C9 | −178.3 (3) | C19—C20—C21—C22 | −0.2 (9) |
C1—Zn1—O4—C9 | −61.1 (4) | C23—N2—C22—C21 | −178.5 (5) |
O4—Zn1—O1—C1 | 169.7 (3) | C23—N2—C22—C17 | 0.7 (5) |
N3—Zn1—O1—C1 | 41.4 (4) | C20—C21—C22—N2 | 179.7 (5) |
O1'—Zn1—O1—C1 | 12.5 (6) | C20—C21—C22—C17 | 0.6 (8) |
N1—Zn1—O1—C1 | −91.2 (3) | C18—C17—C22—N2 | −179.9 (4) |
Zn1—O1—C1—O2 | −7.5 (3) | N1—C17—C22—N2 | −1.0 (5) |
Zn1—O1—C1—C2 | 172.5 (3) | C18—C17—C22—C21 | −0.6 (7) |
O1—C1—C2—C7 | −0.03 (7) | N1—C17—C22—C21 | 178.3 (4) |
O2—C1—C2—C7 | −179.99 (4) | C17—N1—C23—N2 | −0.5 (6) |
Zn1—C1—C2—C7 | 18.3 (8) | Zn1—N1—C23—N2 | 176.6 (3) |
O1—C1—C2—C3 | 180.00 (4) | C22—N2—C23—N1 | −0.1 (6) |
O2—C1—C2—C3 | 0.04 (7) | C30—N3—C24—C25 | 179.3 (5) |
Zn1—C1—C2—C3 | −161.7 (8) | Zn1—N3—C24—C25 | 3.4 (7) |
C6—C5—C8—O3 | 0.04 (9) | C30—N3—C24—C29 | 0.3 (5) |
C4—C5—C8—O3 | −179.97 (5) | Zn1—N3—C24—C29 | −175.6 (3) |
O1—Zn1—O1'—C1' | −6.3 (5) | N3—C24—C25—C26 | 179.9 (5) |
O4—Zn1—O1'—C1' | −36.2 (5) | C29—C24—C25—C26 | −1.2 (8) |
N3—Zn1—O1'—C1' | −163.9 (3) | C24—C25—C26—C27 | −0.5 (9) |
N1—Zn1—O1'—C1' | 82.7 (4) | C25—C26—C27—C28 | 2.2 (10) |
C1—Zn1—O1'—C1' | 43 (3) | C26—C27—C28—C29 | −2.0 (9) |
Zn1—O1'—C1'—O2' | 13.1 (3) | C30—N4—C29—C28 | 179.2 (5) |
Zn1—O1'—C1'—C2' | −166.9 (3) | C30—N4—C29—C24 | −0.2 (5) |
O2'—C1'—C2'—C7' | −0.03 (7) | C27—C28—C29—N4 | −179.1 (5) |
O1'—C1'—C2'—C7' | −179.99 (4) | C27—C28—C29—C24 | 0.3 (7) |
O2'—C1'—C2'—C3' | 180.00 (4) | C25—C24—C29—N4 | −179.1 (4) |
O1'—C1'—C2'—C3' | 0.04 (7) | N3—C24—C29—N4 | 0.0 (5) |
C1'—C2'—C3'—C4' | 179.97 (5) | C25—C24—C29—C28 | 1.4 (7) |
C6'—C5'—C8'—O3' | 0.03 (8) | N3—C24—C29—C28 | −179.5 (4) |
C4'—C5'—C8'—O3' | −179.98 (4) | C24—N3—C30—N4 | −0.5 (5) |
Zn1—O4—C9—O5 | −5.9 (7) | Zn1—N3—C30—N4 | 175.1 (3) |
Zn1—O4—C9—C10 | 174.8 (3) | C29—N4—C30—N3 | 0.5 (5) |
O5—C9—C10—C15 | −10.1 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O1w′i | 0.86 | 2.12 | 2.907 (8) | 152 |
N2—H2n···O1w′ii | 0.86 | 2.17 | 2.960 (8) | 154 |
N4—H4n···O5iii | 0.86 | 2.11 | 2.864 (5) | 145 |
O1w—H1w1···O1 | 0.84 | 2.064 (7) | 2.87 (1) | 159 |
O1w—H1w2···O5 | 0.86 | 1.873 (4) | 2.69 (1) | 157 |
O1w′—H1w3···O5 | 0.86 | 2.353 (4) | 3.112 (8) | 148 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, y−1/2, z; (iii) −x+1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C8H5O3)2(C7H6N2)2].H2O |
Mr | 617.90 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 13.7968 (8), 17.0524 (8), 23.848 (1) |
β (°) | 92.954 (1) |
V (Å3) | 5603.1 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.35 × 0.26 × 0.19 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID IP diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.558, 0.843 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27096, 6393, 3298 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.194, 1.09 |
No. of reflections | 6393 |
No. of parameters | 453 |
No. of restraints | 178 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.67 |
Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O1w'i | 0.86 | 2.12 | 2.907 (8) | 152 |
N2—H2n···O1w'ii | 0.86 | 2.17 | 2.960 (8) | 154 |
N4—H4n···O5iii | 0.86 | 2.11 | 2.864 (5) | 145 |
O1w—H1w1···O1 | 0.84 | 2.064 (7) | 2.87 (1) | 159 |
O1w—H1w2···O5 | 0.86 | 1.873 (4) | 2.69 (1) | 157 |
O1w'—H1w3···O5 | 0.86 | 2.353 (4) | 3.112 (8) | 148 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x−1/2, y−1/2, z; (iii) −x+1/2, −y+3/2, −z+1. |
Bis(4-formylbenzoato)zinc, which exists as a tetrahedral diaqua compound (Deng et al., 2006a), form a five-coordinate aqua complex with phenathroline (Deng et al., 2006b). The title compound is a 1:2 adduct of Bis(4-formylbenzoato)zinc with benzimidazole, crystallizing with a molecule of water (I). The metal center shows tetrahedral coordination (Fig. 1). Adjacent molecules are linked by hydrogen bonds.