Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680706878X/bg2142sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680706878X/bg2142Isup2.hkl |
CCDC reference: 677435
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.002 Å
- R factor = 0.027
- wR factor = 0.080
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn - O1 .. 7.27 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The N-heterocycle was prepared according to reported procedure (Chawla & Gill,1997). Zinc nitrate hexahydrate (0.074 g, 0.25 mmol), 1,3-bis(benzimidazolyl-2-ylmethyl)benzene (0.15 g, 0.5 mmol), acetic acid (2 ml) and water (15 ml) were placed in a 23 ml Teflon-lined stainless steel Parr bomb. The bomb was heated at 433 K for 5 days and cooled to room temperature at 5 K h-1.Colorless block crystals were obtained in 15% yield.
H atoms attached to oxygen and nitrogen were located in the Fourier maps, and refined with restrained N—H = 0.87 Å, O—H = 0.84 Å distances and free isotropic displacement factots. C—H's were placed at geometrically idealized positions with C—H = 0.95 Å (aromatic), 0.98 Å (methyl) and Uiso(H) = 1.2(aromatic), 1.5(methyl)Ueq(C).
Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO (Rigaku 2004); data reduction: RAPID-AUTO (Rigaku 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).
[Zn(C2H3O2)2(C20H14N4)2]·2H2O | F(000) = 1744 |
Mr = 840.19 | Dx = 1.427 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 29371 reflections |
a = 14.1429 (3) Å | θ = 3.1–27.5° |
b = 16.7005 (4) Å | µ = 0.69 mm−1 |
c = 16.5588 (3) Å | T = 153 K |
V = 3911.08 (13) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.29 × 0.26 mm |
Rigaku R-axis SPIDER diffractometer | 4483 independent reflections |
Radiation source: Rotating Anode | 4032 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (Higashi, 1995) | h = −18→18 |
Tmin = 0.761, Tmax = 0.841 | k = −21→21 |
36097 measured reflections | l = −21→20 |
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)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0456P)2 + 1.3144P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4483 reflections | Δρmax = 0.35 e Å−3 |
285 parameters | Δρmin = −0.35 e Å−3 |
4 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (3) |
[Zn(C2H3O2)2(C20H14N4)2]·2H2O | V = 3911.08 (13) Å3 |
Mr = 840.19 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 14.1429 (3) Å | µ = 0.69 mm−1 |
b = 16.7005 (4) Å | T = 153 K |
c = 16.5588 (3) Å | 0.42 × 0.29 × 0.26 mm |
Rigaku R-axis SPIDER diffractometer | 4483 independent reflections |
Absorption correction: multi-scan (Higashi, 1995) | 4032 reflections with I > 2σ(I) |
Tmin = 0.761, Tmax = 0.841 | Rint = 0.022 |
36097 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 4 restraints |
wR(F2) = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.35 e Å−3 |
4483 reflections | Δρmin = −0.35 e Å−3 |
285 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Zn | 0.5000 | 0.200846 (12) | 0.2500 | 0.02036 (8) | |
O1 | 0.43810 (7) | 0.14750 (5) | 0.15455 (5) | 0.0247 (2) | |
O2 | 0.38164 (9) | 0.08183 (6) | 0.25947 (6) | 0.0346 (2) | |
N1 | 0.59696 (7) | 0.27314 (6) | 0.19415 (6) | 0.0199 (2) | |
N2 | 0.65402 (8) | 0.38807 (6) | 0.14616 (6) | 0.0229 (2) | |
N3 | 0.58881 (8) | 0.23678 (7) | 0.50153 (7) | 0.0239 (2) | |
N4 | 0.62077 (8) | 0.34087 (7) | 0.58182 (7) | 0.0270 (2) | |
C1 | 0.62241 (8) | 0.26200 (7) | 0.11345 (7) | 0.0200 (2) | |
C2 | 0.62085 (9) | 0.19356 (8) | 0.06492 (8) | 0.0243 (3) | |
H2 | 0.5999 | 0.1434 | 0.0853 | 0.029* | |
C3 | 0.65122 (10) | 0.20211 (8) | −0.01423 (8) | 0.0287 (3) | |
H3 | 0.6509 | 0.1567 | −0.0488 | 0.034* | |
C4 | 0.68243 (10) | 0.27583 (9) | −0.04472 (8) | 0.0309 (3) | |
H4 | 0.7013 | 0.2794 | −0.0997 | 0.037* | |
C5 | 0.68638 (10) | 0.34315 (8) | 0.00321 (8) | 0.0277 (3) | |
H5 | 0.7083 | 0.3930 | −0.0172 | 0.033* | |
C6 | 0.65670 (9) | 0.33473 (7) | 0.08296 (7) | 0.0220 (2) | |
C7 | 0.61950 (8) | 0.34911 (7) | 0.21111 (7) | 0.0203 (2) | |
C8 | 0.61087 (8) | 0.38614 (7) | 0.29088 (7) | 0.0214 (2) | |
C9 | 0.59900 (9) | 0.46915 (8) | 0.30015 (8) | 0.0252 (3) | |
H9 | 0.5977 | 0.5031 | 0.2541 | 0.030* | |
C10 | 0.58919 (10) | 0.50126 (8) | 0.37704 (9) | 0.0284 (3) | |
H10 | 0.5807 | 0.5573 | 0.3833 | 0.034* | |
C11 | 0.59159 (9) | 0.45248 (8) | 0.44476 (8) | 0.0264 (3) | |
H11 | 0.5852 | 0.4752 | 0.4971 | 0.032* | |
C12 | 0.60338 (9) | 0.36969 (7) | 0.43607 (8) | 0.0223 (2) | |
C13 | 0.60420 (9) | 0.31727 (8) | 0.50712 (8) | 0.0229 (2) | |
C14 | 0.61670 (10) | 0.27139 (8) | 0.62767 (8) | 0.0272 (3) | |
C15 | 0.63182 (12) | 0.26000 (10) | 0.71047 (9) | 0.0375 (3) | |
H15 | 0.6462 | 0.3038 | 0.7450 | 0.045* | |
C16 | 0.62511 (14) | 0.18299 (11) | 0.74009 (9) | 0.0405 (4) | |
H16 | 0.6352 | 0.1738 | 0.7960 | 0.049* | |
C17 | 0.60381 (11) | 0.11817 (9) | 0.69005 (9) | 0.0359 (3) | |
H17 | 0.5993 | 0.0661 | 0.7128 | 0.043* | |
C18 | 0.58912 (10) | 0.12804 (8) | 0.60805 (9) | 0.0305 (3) | |
H18 | 0.5750 | 0.0840 | 0.5738 | 0.037* | |
C19 | 0.59617 (9) | 0.20575 (8) | 0.57840 (8) | 0.0248 (3) | |
C20 | 0.61400 (9) | 0.33772 (7) | 0.35896 (8) | 0.0219 (3) | |
H20 | 0.6236 | 0.2817 | 0.3528 | 0.026* | |
C21 | 0.39227 (9) | 0.08843 (7) | 0.18557 (8) | 0.0236 (3) | |
C22 | 0.35683 (12) | 0.02507 (9) | 0.12828 (9) | 0.0359 (3) | |
H22A | 0.4009 | −0.0202 | 0.1280 | 0.043* | |
H22B | 0.3522 | 0.0475 | 0.0738 | 0.043* | |
H22C | 0.2943 | 0.0067 | 0.1458 | 0.043* | |
H2N | 0.6812 (12) | 0.4349 (7) | 0.1461 (11) | 0.043 (5)* | |
H3N | 0.5746 (13) | 0.2099 (9) | 0.4590 (8) | 0.038 (5)* | |
O3 | 0.73576 (9) | 0.53271 (6) | 0.13461 (7) | 0.0396 (3) | |
H3AO | 0.7035 (13) | 0.5725 (9) | 0.1205 (12) | 0.055 (6)* | |
H3BO | 0.7795 (12) | 0.5466 (12) | 0.1658 (11) | 0.057 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.02511 (12) | 0.01605 (12) | 0.01992 (12) | 0.000 | 0.00432 (7) | 0.000 |
O1 | 0.0304 (5) | 0.0176 (4) | 0.0262 (5) | −0.0038 (3) | 0.0034 (4) | 0.0008 (3) |
O2 | 0.0477 (6) | 0.0271 (5) | 0.0291 (5) | −0.0057 (5) | 0.0114 (4) | 0.0010 (4) |
N1 | 0.0221 (5) | 0.0175 (5) | 0.0201 (5) | −0.0003 (4) | 0.0027 (4) | −0.0001 (4) |
N2 | 0.0252 (5) | 0.0195 (5) | 0.0239 (5) | −0.0036 (4) | −0.0017 (4) | 0.0035 (4) |
N3 | 0.0279 (6) | 0.0229 (5) | 0.0208 (5) | −0.0006 (4) | −0.0004 (4) | −0.0012 (4) |
N4 | 0.0323 (6) | 0.0267 (6) | 0.0219 (5) | −0.0011 (4) | −0.0026 (4) | −0.0012 (4) |
C1 | 0.0184 (5) | 0.0218 (6) | 0.0196 (6) | 0.0018 (4) | 0.0014 (4) | 0.0022 (5) |
C2 | 0.0241 (6) | 0.0228 (6) | 0.0260 (6) | 0.0022 (5) | 0.0035 (5) | −0.0003 (5) |
C3 | 0.0284 (7) | 0.0333 (7) | 0.0243 (6) | 0.0048 (5) | 0.0026 (5) | −0.0045 (5) |
C4 | 0.0289 (7) | 0.0421 (8) | 0.0216 (6) | 0.0030 (6) | 0.0033 (5) | 0.0035 (6) |
C5 | 0.0276 (6) | 0.0318 (7) | 0.0237 (6) | −0.0022 (5) | 0.0004 (5) | 0.0090 (5) |
C6 | 0.0205 (6) | 0.0229 (6) | 0.0226 (6) | −0.0001 (5) | −0.0016 (5) | 0.0030 (5) |
C7 | 0.0200 (5) | 0.0182 (5) | 0.0227 (6) | 0.0001 (4) | −0.0008 (5) | 0.0020 (5) |
C8 | 0.0205 (6) | 0.0202 (6) | 0.0236 (6) | −0.0015 (4) | −0.0018 (5) | −0.0015 (5) |
C9 | 0.0278 (6) | 0.0191 (6) | 0.0287 (6) | −0.0012 (5) | −0.0045 (5) | 0.0013 (5) |
C10 | 0.0335 (7) | 0.0187 (6) | 0.0332 (7) | 0.0014 (5) | −0.0055 (6) | −0.0043 (5) |
C11 | 0.0288 (6) | 0.0240 (6) | 0.0263 (6) | 0.0019 (5) | −0.0022 (5) | −0.0063 (5) |
C12 | 0.0211 (6) | 0.0219 (6) | 0.0239 (6) | −0.0001 (4) | −0.0022 (5) | −0.0009 (5) |
C13 | 0.0219 (6) | 0.0233 (6) | 0.0233 (6) | 0.0009 (5) | −0.0011 (5) | −0.0023 (5) |
C14 | 0.0276 (7) | 0.0285 (7) | 0.0255 (6) | −0.0005 (5) | −0.0012 (5) | 0.0005 (5) |
C15 | 0.0499 (9) | 0.0384 (8) | 0.0241 (7) | −0.0034 (7) | −0.0054 (6) | −0.0009 (6) |
C16 | 0.0507 (10) | 0.0463 (9) | 0.0246 (7) | 0.0003 (8) | −0.0030 (6) | 0.0074 (6) |
C17 | 0.0404 (8) | 0.0334 (7) | 0.0338 (7) | 0.0027 (6) | 0.0038 (6) | 0.0093 (6) |
C18 | 0.0341 (7) | 0.0260 (6) | 0.0313 (7) | 0.0015 (5) | 0.0036 (6) | 0.0016 (6) |
C19 | 0.0224 (6) | 0.0287 (6) | 0.0234 (6) | 0.0013 (5) | 0.0013 (5) | 0.0016 (5) |
C20 | 0.0229 (6) | 0.0182 (6) | 0.0246 (6) | −0.0002 (4) | −0.0018 (5) | −0.0016 (5) |
C21 | 0.0241 (6) | 0.0177 (6) | 0.0290 (6) | 0.0003 (4) | 0.0019 (5) | 0.0022 (5) |
C22 | 0.0432 (9) | 0.0275 (7) | 0.0370 (8) | −0.0092 (6) | −0.0095 (6) | 0.0003 (6) |
O3 | 0.0458 (7) | 0.0217 (5) | 0.0511 (7) | −0.0099 (5) | −0.0215 (5) | 0.0115 (5) |
Zn—O1 | 2.0145 (9) | C8—C20 | 1.3880 (17) |
Zn—O1i | 2.0145 (9) | C8—C9 | 1.4047 (17) |
Zn—N1 | 2.0477 (10) | C9—C10 | 1.3886 (19) |
Zn—N1i | 2.0477 (10) | C9—H9 | 0.9500 |
O1—C21 | 1.2873 (15) | C10—C11 | 1.386 (2) |
O2—C21 | 1.2378 (16) | C10—H10 | 0.9500 |
N1—C7 | 1.3380 (16) | C11—C12 | 1.4001 (17) |
N1—C1 | 1.3964 (15) | C11—H11 | 0.9500 |
N2—C7 | 1.3485 (16) | C12—C20 | 1.3923 (17) |
N2—C6 | 1.3748 (16) | C12—C13 | 1.4664 (18) |
N2—H2N | 0.871 (9) | C14—C19 | 1.3970 (19) |
N3—C13 | 1.3649 (16) | C14—C15 | 1.4006 (19) |
N3—C19 | 1.3782 (17) | C15—C16 | 1.380 (2) |
N3—H3N | 0.858 (9) | C15—H15 | 0.9500 |
N4—C13 | 1.3193 (17) | C16—C17 | 1.396 (2) |
N4—C14 | 1.3878 (17) | C16—H16 | 0.9500 |
C1—C2 | 1.3974 (17) | C17—C18 | 1.384 (2) |
C1—C6 | 1.4020 (17) | C17—H17 | 0.9500 |
C2—C3 | 1.3867 (19) | C18—C19 | 1.3912 (19) |
C2—H2 | 0.9500 | C18—H18 | 0.9500 |
C3—C4 | 1.402 (2) | C20—H20 | 0.9500 |
C3—H3 | 0.9500 | C21—C22 | 1.5069 (18) |
C4—C5 | 1.377 (2) | C22—H22A | 0.9800 |
C4—H4 | 0.9500 | C22—H22B | 0.9800 |
C5—C6 | 1.3928 (18) | C22—H22C | 0.9800 |
C5—H5 | 0.9500 | O3—H3AO | 0.839 (9) |
C7—C8 | 1.4636 (17) | O3—H3BO | 0.839 (9) |
O1—Zn—O1i | 127.50 (5) | C11—C10—C9 | 120.81 (12) |
O1—Zn—N1 | 101.39 (4) | C11—C10—H10 | 119.6 |
O1i—Zn—N1 | 108.91 (4) | C9—C10—H10 | 119.6 |
O1—Zn—N1i | 108.91 (4) | C10—C11—C12 | 120.01 (12) |
O1i—Zn—N1i | 101.39 (4) | C10—C11—H11 | 120.0 |
N1—Zn—N1i | 107.74 (6) | C12—C11—H11 | 120.0 |
C21—O1—Zn | 104.16 (8) | C20—C12—C11 | 119.07 (12) |
C7—N1—C1 | 105.41 (10) | C20—C12—C13 | 120.39 (11) |
C7—N1—Zn | 128.60 (8) | C11—C12—C13 | 120.54 (12) |
C1—N1—Zn | 121.75 (8) | N4—C13—N3 | 112.71 (12) |
C7—N2—C6 | 107.73 (10) | N4—C13—C12 | 125.12 (12) |
C7—N2—H2N | 126.4 (12) | N3—C13—C12 | 122.16 (11) |
C6—N2—H2N | 124.6 (12) | N4—C14—C19 | 110.20 (12) |
C13—N3—C19 | 107.19 (11) | N4—C14—C15 | 130.00 (13) |
C13—N3—H3N | 127.4 (12) | C19—C14—C15 | 119.79 (13) |
C19—N3—H3N | 125.3 (12) | C16—C15—C14 | 117.66 (14) |
C13—N4—C14 | 104.82 (11) | C16—C15—H15 | 121.2 |
N1—C1—C2 | 130.94 (11) | C14—C15—H15 | 121.2 |
N1—C1—C6 | 108.57 (11) | C15—C16—C17 | 121.78 (14) |
C2—C1—C6 | 120.46 (11) | C15—C16—H16 | 119.1 |
C3—C2—C1 | 117.04 (12) | C17—C16—H16 | 119.1 |
C3—C2—H2 | 121.5 | C18—C17—C16 | 121.50 (14) |
C1—C2—H2 | 121.5 | C18—C17—H17 | 119.3 |
C2—C3—C4 | 121.89 (13) | C16—C17—H17 | 119.3 |
C2—C3—H3 | 119.1 | C17—C18—C19 | 116.54 (14) |
C4—C3—H3 | 119.1 | C17—C18—H18 | 121.7 |
C5—C4—C3 | 121.48 (12) | C19—C18—H18 | 121.7 |
C5—C4—H4 | 119.3 | N3—C19—C18 | 132.16 (13) |
C3—C4—H4 | 119.3 | N3—C19—C14 | 105.07 (11) |
C4—C5—C6 | 116.86 (12) | C18—C19—C14 | 122.74 (13) |
C4—C5—H5 | 121.6 | C8—C20—C12 | 121.19 (11) |
C6—C5—H5 | 121.6 | C8—C20—H20 | 119.4 |
N2—C6—C5 | 131.66 (12) | C12—C20—H20 | 119.4 |
N2—C6—C1 | 106.12 (11) | O2—C21—O1 | 121.59 (12) |
C5—C6—C1 | 122.22 (12) | O2—C21—C22 | 121.30 (12) |
N1—C7—N2 | 112.11 (11) | O1—C21—C22 | 117.02 (12) |
N1—C7—C8 | 124.76 (11) | C21—C22—H22A | 109.5 |
N2—C7—C8 | 123.11 (11) | C21—C22—H22B | 109.5 |
C20—C8—C9 | 119.35 (11) | H22A—C22—H22B | 109.5 |
C20—C8—C7 | 118.95 (11) | C21—C22—H22C | 109.5 |
C9—C8—C7 | 121.70 (12) | H22A—C22—H22C | 109.5 |
C10—C9—C8 | 119.55 (12) | H22B—C22—H22C | 109.5 |
C10—C9—H9 | 120.2 | H3AO—O3—H3BO | 110.7 (19) |
C8—C9—H9 | 120.2 | ||
O1i—Zn—O1—C21 | 40.82 (7) | C20—C8—C9—C10 | −0.95 (19) |
N1—Zn—O1—C21 | 165.66 (8) | C7—C8—C9—C10 | 178.68 (12) |
N1i—Zn—O1—C21 | −80.92 (8) | C8—C9—C10—C11 | 0.4 (2) |
O1—Zn—N1—C7 | 137.44 (10) | C9—C10—C11—C12 | −0.4 (2) |
O1i—Zn—N1—C7 | −86.05 (11) | C10—C11—C12—C20 | 0.97 (19) |
N1i—Zn—N1—C7 | 23.14 (9) | C10—C11—C12—C13 | −178.81 (12) |
O1—Zn—N1—C1 | −15.92 (10) | C14—N4—C13—N3 | 0.51 (15) |
O1i—Zn—N1—C1 | 120.59 (9) | C14—N4—C13—C12 | −178.52 (12) |
N1i—Zn—N1—C1 | −130.22 (10) | C19—N3—C13—N4 | −0.16 (15) |
C7—N1—C1—C2 | 175.43 (13) | C19—N3—C13—C12 | 178.90 (11) |
Zn—N1—C1—C2 | −25.88 (18) | C20—C12—C13—N4 | 160.33 (13) |
C7—N1—C1—C6 | −2.48 (13) | C11—C12—C13—N4 | −19.9 (2) |
Zn—N1—C1—C6 | 156.20 (8) | C20—C12—C13—N3 | −18.61 (18) |
N1—C1—C2—C3 | −179.94 (13) | C11—C12—C13—N3 | 161.17 (12) |
C6—C1—C2—C3 | −2.24 (19) | C13—N4—C14—C19 | −0.68 (15) |
C1—C2—C3—C4 | 0.1 (2) | C13—N4—C14—C15 | 177.69 (15) |
C2—C3—C4—C5 | 1.5 (2) | N4—C14—C15—C16 | −178.56 (15) |
C3—C4—C5—C6 | −0.9 (2) | C19—C14—C15—C16 | −0.3 (2) |
C7—N2—C6—C5 | −179.54 (13) | C14—C15—C16—C17 | −0.2 (3) |
C7—N2—C6—C1 | −0.20 (13) | C15—C16—C17—C18 | 0.5 (3) |
C4—C5—C6—N2 | 177.96 (13) | C16—C17—C18—C19 | −0.3 (2) |
C4—C5—C6—C1 | −1.29 (19) | C13—N3—C19—C18 | −178.53 (14) |
N1—C1—C6—N2 | 1.67 (13) | C13—N3—C19—C14 | −0.26 (14) |
C2—C1—C6—N2 | −176.50 (11) | C17—C18—C19—N3 | 177.85 (14) |
N1—C1—C6—C5 | −178.92 (12) | C17—C18—C19—C14 | −0.2 (2) |
C2—C1—C6—C5 | 2.91 (19) | N4—C14—C19—N3 | 0.59 (15) |
C1—N1—C7—N2 | 2.43 (14) | C15—C14—C19—N3 | −177.97 (13) |
Zn—N1—C7—N2 | −154.27 (9) | N4—C14—C19—C18 | 179.06 (13) |
C1—N1—C7—C8 | −175.89 (11) | C15—C14—C19—C18 | 0.5 (2) |
Zn—N1—C7—C8 | 27.41 (17) | C9—C8—C20—C12 | 1.52 (18) |
C6—N2—C7—N1 | −1.44 (14) | C7—C8—C20—C12 | −178.12 (11) |
C6—N2—C7—C8 | 176.92 (11) | C11—C12—C20—C8 | −1.53 (19) |
N1—C7—C8—C20 | 25.18 (18) | C13—C12—C20—C8 | 178.26 (12) |
N2—C7—C8—C20 | −152.96 (12) | Zn—O1—C21—O2 | 10.67 (15) |
N1—C7—C8—C9 | −154.45 (12) | Zn—O1—C21—C22 | −165.93 (10) |
N2—C7—C8—C9 | 27.41 (18) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O3 | 0.87 (1) | 1.82 (1) | 2.6848 (14) | 174 (2) |
N3—H3N···O1i | 0.86 (1) | 2.16 (1) | 3.0079 (14) | 171 (2) |
O3—H3AO···N4ii | 0.84 (1) | 1.97 (1) | 2.8046 (16) | 175 (2) |
O3—H3BO···O2iii | 0.84 (1) | 1.99 (1) | 2.8295 (15) | 179 (2) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+1, z−1/2; (iii) x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C2H3O2)2(C20H14N4)2]·2H2O |
Mr | 840.19 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 153 |
a, b, c (Å) | 14.1429 (3), 16.7005 (4), 16.5588 (3) |
V (Å3) | 3911.08 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.42 × 0.29 × 0.26 |
Data collection | |
Diffractometer | Rigaku R-axis SPIDER diffractometer |
Absorption correction | Multi-scan (Higashi, 1995) |
Tmin, Tmax | 0.761, 0.841 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36097, 4483, 4032 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.080, 1.06 |
No. of reflections | 4483 |
No. of parameters | 285 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.35 |
Computer programs: RAPID-AUTO (Rigaku 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O3 | 0.871 (9) | 1.817 (9) | 2.6848 (14) | 174.0 (17) |
N3—H3N···O1i | 0.858 (9) | 2.158 (10) | 3.0079 (14) | 170.6 (17) |
O3—H3AO···N4ii | 0.839 (9) | 1.968 (10) | 2.8046 (16) | 175 (2) |
O3—H3BO···O2iii | 0.839 (9) | 1.991 (10) | 2.8295 (15) | 179 (2) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x, −y+1, z−1/2; (iii) x+1/2, y+1/2, −z+1/2. |
Benzimidazolyl derivatives and their transition metal complexes have been extensively investigated (Shivakumaraiah et al., 2003). In previous works zinc terephthalate and zinc succinate adducts of 1,3-bis(benzimidazol-2-ylmethyl)benzene have been reported (Meng et al., 2007; Meng et al., 2007). The present work reports the crystal structure of [Zn(ac)2(L)2].2H2O, (I), where L is 1,3-bis(benzimidazol-2-ylmethyl)benzene and ac is the acetate ion, which assumes a similar geometry to previously reported complexes in the literature (Meng et al., 2007). (shown in scheme I). The crystal structure of (I) consists of the mononuclear zinc(II) complex and solvato water molecules (Fig. 1). The Zn atom is four-coordinate with two N atoms and two O atoms from the 1,3-bis(benzimidazol-2- ylmethyl)benzene and the acetate ligands, respectively. (Zn—O: 2.0145 (9) Å, Zn—N: 2.0477 (10) Å, coordination angle range: 101.39 (4)- 127.50 (5) °.). The complex and solvent water molecules are connected via O—H···N, O—H···O and N—H···O hydrogen bonds to form a three-dimensional network (Table 1).