Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018570/lh2363sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018570/lh2363Isup2.hkl |
CCDC reference: 646636
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.130
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.782 0.877 RT(exp) = 1.121 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.13 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
0 ALERT level A = In general: serious problem 0 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
For related literature, see: Albada et al. (1995); Roderick et al. (1972); Wang & Joullie (1957), Allen et al. (1987); Sun et al. (2004).
The ligand 1,3-bis(2-benzimidazolyl)propane (dbz) was synthesized from reported literature earlier (van Albada et al., 1995; Wang
& Joullie, 1957). The title compound was prepared according to the following procedure: The ligand (0.28 g, 1 mmol) in 10 ml me thanol was added slowly to a Cu(NO3)2.2H2O (0.12 g, 0.5 mmol) solution of 10 ml me thanol. The mixture was stirred for 1 h. After filtration, the brownish solution was allowed to stand at room temperature. Green block-shaped crystals of (I) were obtained after three weeks.
H atoms bonded to O and N atoms were located in difference maps and then included in the refinement with bond-length restraints of O–H = 0.82 Å and N–H = 0.78 Å, with Uiso(H)= 1.2Ueq (O) and the Uiso(H) of the N—H atoms refined. H atoms bonded to C atoms were placed in calculated positions and included in the riding-model approximation, with C–H = 0.97—0.98 Å and U iso(H) = 1.2Ueq(C of methylene and aromatic) or 1.5U eq(C of methyl).
Interest in bis(2-benzimidazolyl)alkanes is widespread, due to their wide-ranging antiviral activity (Roderick et al., 1972). Herein, we report the crystal structure of the title compound (I). In the cation (Fig. 1), the CuII ion lies on a crystallogrphic twofold axis. Hence, the CuII ion is coordinated by four N atoms (N1, N3, N1a, N3a [symmety code: (a) 1/2 - x, 3/2 - y, z]) from two dbz ligangs. The bond anlges listed in Table 1 indicate a distorted square-planar coordination geomtry.
In the crystal structure, molecules are linked by N—Hbenzimidazole···Onitrate and O—Hmethanol···O nitrate hydrogen bonds, forming a two-dimensional framework structure perpendicular to the ab plane (Table 2, Fig. 2).
For related literature, see: Albada et al. (1995); Roderick et al. (1972); Wang & Joullie (1957), Allen et al. (1987); Sun et al. (2004).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Cu(C17H16N4)2](NO3)2·2C2H6O | F(000) = 1676 |
Mr = 804.32 | Dx = 1.441 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 5026 reflections |
a = 14.4793 (10) Å | θ = 2.3–25.4° |
b = 17.8978 (13) Å | µ = 0.66 mm−1 |
c = 14.3078 (10) Å | T = 297 K |
V = 3707.8 (5) Å3 | Block, green |
Z = 4 | 0.45 × 0.32 × 0.20 mm |
Bruker APEX CCD diffractometer | 3394 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
φ and ω scans | h = −19→18 |
23966 measured reflections | k = −21→23 |
4453 independent reflections | l = −17→18 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0635P)2 + 1.4161P] where P = (Fo2 + 2Fc2)/3 |
4453 reflections | (Δ/σ)max = 0.001 |
261 parameters | Δρmax = 0.48 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
[Cu(C17H16N4)2](NO3)2·2C2H6O | V = 3707.8 (5) Å3 |
Mr = 804.32 | Z = 4 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 14.4793 (10) Å | µ = 0.66 mm−1 |
b = 17.8978 (13) Å | T = 297 K |
c = 14.3078 (10) Å | 0.45 × 0.32 × 0.20 mm |
Bruker APEX CCD diffractometer | 3394 reflections with I > 2σ(I) |
23966 measured reflections | Rint = 0.042 |
4453 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 1 restraint |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.48 e Å−3 |
4453 reflections | Δρmin = −0.25 e Å−3 |
261 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 | ||
H4N | 0.293 (2) | 0.4833 (17) | 0.041 (2) | 0.048 (8)* | |
H2N | −0.077 (2) | 0.6948 (16) | 0.111 (2) | 0.048 (8)* | |
Cu1 | 0.2500 | 0.7500 | 0.06676 (3) | 0.03171 (13) | |
N1 | 0.11849 (13) | 0.74057 (10) | 0.10902 (14) | 0.0352 (4) | |
N3 | 0.27403 (13) | 0.64615 (10) | 0.02440 (14) | 0.0342 (4) | |
C1 | 0.07694 (16) | 0.79298 (12) | 0.16863 (16) | 0.0368 (5) | |
C2 | 0.1142 (2) | 0.85029 (14) | 0.22291 (17) | 0.0449 (6) | |
H2 | 0.1773 | 0.8601 | 0.2228 | 0.054* | |
C3 | 0.0542 (2) | 0.89193 (15) | 0.2768 (2) | 0.0554 (7) | |
H3 | 0.0774 | 0.9310 | 0.3127 | 0.067* | |
C4 | −0.0399 (2) | 0.87695 (17) | 0.2789 (2) | 0.0619 (8) | |
H4 | −0.0782 | 0.9062 | 0.3162 | 0.074* | |
C5 | −0.0778 (2) | 0.82015 (17) | 0.2275 (2) | 0.0562 (7) | |
H5 | −0.1407 | 0.8098 | 0.2294 | 0.067* | |
C6 | −0.01757 (17) | 0.77856 (15) | 0.17211 (18) | 0.0430 (6) | |
C7 | 0.04996 (16) | 0.69688 (13) | 0.07935 (16) | 0.0371 (5) | |
C8 | 0.05757 (17) | 0.62941 (14) | 0.01904 (18) | 0.0434 (6) | |
H8A | 0.1047 | 0.6377 | −0.0280 | 0.052* | |
H8B | −0.0007 | 0.6213 | −0.0129 | 0.052* | |
C9 | 0.08211 (18) | 0.55980 (13) | 0.07567 (19) | 0.0465 (6) | |
H9A | 0.0857 | 0.5173 | 0.0338 | 0.056* | |
H9B | 0.0331 | 0.5501 | 0.1203 | 0.056* | |
C10 | 0.17360 (16) | 0.56732 (13) | 0.12819 (17) | 0.0405 (5) | |
H10A | 0.1698 | 0.6085 | 0.1721 | 0.049* | |
H10B | 0.1856 | 0.5220 | 0.1633 | 0.049* | |
C11 | 0.25044 (16) | 0.58083 (13) | 0.06119 (16) | 0.0371 (5) | |
C12 | 0.36087 (17) | 0.55352 (13) | −0.03919 (17) | 0.0396 (5) | |
C13 | 0.4271 (2) | 0.52029 (15) | −0.09541 (19) | 0.0516 (7) | |
H13 | 0.4376 | 0.4690 | −0.0940 | 0.062* | |
C14 | 0.4766 (2) | 0.56670 (17) | −0.1534 (2) | 0.0568 (7) | |
H14 | 0.5219 | 0.5465 | −0.1918 | 0.068* | |
C15 | 0.4603 (2) | 0.64322 (17) | −0.1558 (2) | 0.0543 (7) | |
H15 | 0.4951 | 0.6729 | −0.1959 | 0.065* | |
C16 | 0.39374 (18) | 0.67644 (14) | −0.10034 (18) | 0.0465 (6) | |
H16 | 0.3825 | 0.7275 | −0.1030 | 0.056* | |
C17 | 0.34427 (16) | 0.63005 (13) | −0.04022 (16) | 0.0363 (5) | |
C18 | 0.1719 (4) | 0.1726 (3) | 0.0359 (4) | 0.1238 (19) | |
H18A | 0.1675 | 0.2185 | 0.0705 | 0.186* | |
H18B | 0.1110 | 0.1540 | 0.0232 | 0.186* | |
H18C | 0.2035 | 0.1816 | −0.0221 | 0.186* | |
N2 | −0.03139 (15) | 0.71824 (13) | 0.11500 (16) | 0.0444 (5) | |
N4 | 0.30001 (15) | 0.52477 (12) | 0.02574 (16) | 0.0423 (5) | |
N5 | 0.81550 (16) | 0.58786 (18) | 0.1762 (2) | 0.0654 (7) | |
O1 | 0.7826 (3) | 0.53217 (18) | 0.2119 (3) | 0.1170 (11) | |
O2 | 0.81605 (17) | 0.64741 (15) | 0.2217 (2) | 0.0854 (7) | |
O3 | 0.84823 (19) | 0.58743 (19) | 0.0982 (2) | 0.1039 (10) | |
O4 | 0.2211 (2) | 0.11977 (14) | 0.08836 (19) | 0.0816 (7) | |
H4A | 0.216 (4) | 0.122 (3) | 0.1451 (8) | 0.122* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0331 (2) | 0.0260 (2) | 0.0361 (2) | −0.00241 (15) | 0.000 | 0.000 |
N1 | 0.0356 (10) | 0.0323 (10) | 0.0376 (10) | −0.0013 (8) | 0.0028 (8) | 0.0005 (8) |
N3 | 0.0372 (10) | 0.0273 (9) | 0.0380 (10) | −0.0017 (7) | 0.0034 (8) | −0.0023 (8) |
C1 | 0.0435 (13) | 0.0311 (12) | 0.0357 (12) | 0.0029 (9) | 0.0047 (9) | 0.0073 (9) |
C2 | 0.0571 (16) | 0.0381 (13) | 0.0395 (13) | −0.0006 (11) | 0.0073 (11) | 0.0030 (11) |
C3 | 0.084 (2) | 0.0397 (14) | 0.0424 (15) | 0.0062 (14) | 0.0068 (14) | 0.0015 (11) |
C4 | 0.075 (2) | 0.0527 (17) | 0.0581 (18) | 0.0256 (15) | 0.0183 (15) | 0.0057 (14) |
C5 | 0.0488 (15) | 0.0561 (17) | 0.0636 (18) | 0.0159 (13) | 0.0125 (13) | 0.0094 (14) |
C6 | 0.0441 (14) | 0.0407 (13) | 0.0441 (14) | 0.0063 (11) | 0.0030 (10) | 0.0098 (11) |
C7 | 0.0365 (12) | 0.0381 (12) | 0.0367 (12) | −0.0029 (10) | −0.0020 (9) | 0.0079 (10) |
C8 | 0.0415 (13) | 0.0463 (14) | 0.0425 (14) | −0.0091 (11) | −0.0029 (10) | −0.0071 (11) |
C9 | 0.0459 (14) | 0.0346 (13) | 0.0589 (16) | −0.0109 (11) | 0.0082 (11) | −0.0028 (11) |
C10 | 0.0464 (14) | 0.0302 (12) | 0.0448 (14) | −0.0018 (10) | 0.0081 (10) | 0.0029 (10) |
C11 | 0.0404 (12) | 0.0317 (11) | 0.0391 (12) | −0.0022 (10) | −0.0016 (10) | −0.0015 (9) |
C12 | 0.0442 (13) | 0.0341 (12) | 0.0407 (13) | −0.0009 (10) | 0.0020 (10) | −0.0012 (10) |
C13 | 0.0596 (17) | 0.0414 (14) | 0.0540 (16) | 0.0069 (12) | 0.0091 (13) | −0.0075 (12) |
C14 | 0.0592 (17) | 0.0622 (18) | 0.0491 (16) | 0.0052 (14) | 0.0167 (13) | −0.0060 (14) |
C15 | 0.0610 (17) | 0.0585 (17) | 0.0434 (14) | −0.0055 (14) | 0.0155 (13) | 0.0019 (13) |
C16 | 0.0572 (16) | 0.0381 (13) | 0.0441 (14) | −0.0047 (11) | 0.0067 (12) | 0.0026 (11) |
C17 | 0.0391 (12) | 0.0349 (12) | 0.0348 (12) | −0.0031 (10) | 0.0006 (9) | −0.0024 (9) |
C18 | 0.140 (5) | 0.074 (3) | 0.158 (5) | 0.013 (3) | 0.034 (4) | 0.030 (3) |
N2 | 0.0335 (12) | 0.0476 (12) | 0.0521 (13) | −0.0011 (10) | −0.0017 (9) | 0.0090 (11) |
N4 | 0.0517 (13) | 0.0253 (10) | 0.0498 (12) | −0.0002 (9) | 0.0078 (10) | −0.0003 (9) |
N5 | 0.0395 (13) | 0.0756 (19) | 0.081 (2) | −0.0106 (13) | −0.0033 (13) | 0.0111 (16) |
O1 | 0.133 (3) | 0.084 (2) | 0.134 (3) | −0.032 (2) | 0.020 (2) | 0.025 (2) |
O2 | 0.0706 (16) | 0.0768 (17) | 0.109 (2) | −0.0088 (13) | 0.0124 (14) | 0.0026 (16) |
O3 | 0.0819 (18) | 0.147 (3) | 0.0829 (19) | −0.0447 (18) | 0.0125 (15) | −0.0126 (18) |
O4 | 0.114 (2) | 0.0473 (13) | 0.0834 (17) | 0.0018 (13) | 0.0006 (16) | −0.0110 (13) |
Cu1—N3 | 1.9857 (18) | C9—H9B | 0.9700 |
Cu1—N3i | 1.9857 (18) | C10—C11 | 1.488 (3) |
Cu1—N1 | 2.0049 (19) | C10—H10A | 0.9700 |
Cu1—N1i | 2.0049 (19) | C10—H10B | 0.9700 |
N1—C7 | 1.333 (3) | C11—N4 | 1.334 (3) |
N1—C1 | 1.403 (3) | C12—N4 | 1.380 (3) |
N3—C11 | 1.327 (3) | C12—C13 | 1.386 (4) |
N3—C17 | 1.404 (3) | C12—C17 | 1.391 (3) |
C1—C6 | 1.393 (3) | C13—C14 | 1.375 (4) |
C1—C2 | 1.395 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.380 (4) | C14—C15 | 1.390 (4) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.390 (5) | C15—C16 | 1.382 (4) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.369 (5) | C16—C17 | 1.394 (3) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.393 (4) | C18—O4 | 1.403 (5) |
C5—H5 | 0.9300 | C18—H18A | 0.9600 |
C6—N2 | 1.369 (4) | C18—H18B | 0.9600 |
C7—N2 | 1.339 (3) | C18—H18C | 0.9600 |
C7—C8 | 1.488 (3) | N2—H2N | 0.78 (3) |
C8—C9 | 1.528 (4) | N4—H4N | 0.78 (3) |
C8—H8A | 0.9700 | N5—O3 | 1.213 (4) |
C8—H8B | 0.9700 | N5—O1 | 1.217 (4) |
C9—C10 | 1.529 (4) | N5—O2 | 1.249 (4) |
C9—H9A | 0.9700 | O4—H4A | 0.816 (10) |
N3—Cu1—N3i | 144.46 (12) | H9A—C9—H9B | 107.8 |
N3—Cu1—N1 | 100.35 (7) | C11—C10—C9 | 110.2 (2) |
N3i—Cu1—N1 | 90.25 (7) | C11—C10—H10A | 109.6 |
N3—Cu1—N1i | 90.25 (7) | C9—C10—H10A | 109.6 |
N3i—Cu1—N1i | 100.35 (7) | C11—C10—H10B | 109.6 |
N1—Cu1—N1i | 144.89 (11) | C9—C10—H10B | 109.6 |
C7—N1—C1 | 105.46 (19) | H10A—C10—H10B | 108.1 |
C7—N1—Cu1 | 131.33 (16) | N3—C11—N4 | 111.9 (2) |
C1—N1—Cu1 | 122.29 (15) | N3—C11—C10 | 126.2 (2) |
C11—N3—C17 | 105.48 (19) | N4—C11—C10 | 121.7 (2) |
C11—N3—Cu1 | 131.19 (16) | N4—C12—C13 | 132.3 (2) |
C17—N3—Cu1 | 121.32 (15) | N4—C12—C17 | 105.3 (2) |
C6—C1—C2 | 119.8 (2) | C13—C12—C17 | 122.4 (2) |
C6—C1—N1 | 108.6 (2) | C14—C13—C12 | 116.8 (2) |
C2—C1—N1 | 131.6 (2) | C14—C13—H13 | 121.6 |
C3—C2—C1 | 117.7 (3) | C12—C13—H13 | 121.6 |
C3—C2—H2 | 121.2 | C13—C14—C15 | 121.4 (3) |
C1—C2—H2 | 121.2 | C13—C14—H14 | 119.3 |
C2—C3—C4 | 121.7 (3) | C15—C14—H14 | 119.3 |
C2—C3—H3 | 119.2 | C16—C15—C14 | 121.9 (3) |
C4—C3—H3 | 119.2 | C16—C15—H15 | 119.1 |
C5—C4—C3 | 121.6 (3) | C14—C15—H15 | 119.1 |
C5—C4—H4 | 119.2 | C15—C16—C17 | 117.1 (2) |
C3—C4—H4 | 119.2 | C15—C16—H16 | 121.4 |
C4—C5—C6 | 116.9 (3) | C17—C16—H16 | 121.4 |
C4—C5—H5 | 121.6 | C12—C17—C16 | 120.3 (2) |
C6—C5—H5 | 121.6 | C12—C17—N3 | 108.7 (2) |
N2—C6—C5 | 132.0 (3) | C16—C17—N3 | 131.0 (2) |
N2—C6—C1 | 105.6 (2) | O4—C18—H18A | 109.5 |
C5—C6—C1 | 122.4 (3) | O4—C18—H18B | 109.5 |
N1—C7—N2 | 111.5 (2) | H18A—C18—H18B | 109.5 |
N1—C7—C8 | 127.3 (2) | O4—C18—H18C | 109.5 |
N2—C7—C8 | 121.2 (2) | H18A—C18—H18C | 109.5 |
C7—C8—C9 | 111.8 (2) | H18B—C18—H18C | 109.5 |
C7—C8—H8A | 109.3 | C7—N2—C6 | 108.9 (2) |
C9—C8—H8A | 109.3 | C7—N2—H2N | 124 (2) |
C7—C8—H8B | 109.3 | C6—N2—H2N | 126 (2) |
C9—C8—H8B | 109.3 | C11—N4—C12 | 108.6 (2) |
H8A—C8—H8B | 107.9 | C11—N4—H4N | 123 (2) |
C8—C9—C10 | 112.97 (19) | C12—N4—H4N | 128 (2) |
C8—C9—H9A | 109.0 | O3—N5—O1 | 122.3 (4) |
C10—C9—H9A | 109.0 | O3—N5—O2 | 118.9 (3) |
C8—C9—H9B | 109.0 | O1—N5—O2 | 118.9 (3) |
C10—C9—H9B | 109.0 | C18—O4—H4A | 117 (4) |
N3—Cu1—N1—C7 | −30.8 (2) | N2—C7—C8—C9 | −93.1 (3) |
N3i—Cu1—N1—C7 | 115.1 (2) | C7—C8—C9—C10 | −59.3 (3) |
N1i—Cu1—N1—C7 | −136.3 (2) | C8—C9—C10—C11 | −59.8 (3) |
N3—Cu1—N1—C1 | 161.87 (17) | C17—N3—C11—N4 | 0.3 (3) |
N3i—Cu1—N1—C1 | −52.24 (18) | Cu1—N3—C11—N4 | −163.27 (17) |
N1i—Cu1—N1—C1 | 56.35 (16) | C17—N3—C11—C10 | −174.9 (2) |
N3i—Cu1—N3—C11 | −146.5 (2) | Cu1—N3—C11—C10 | 21.5 (4) |
N1—Cu1—N3—C11 | −41.2 (2) | C9—C10—C11—N3 | 82.5 (3) |
N1i—Cu1—N3—C11 | 105.1 (2) | C9—C10—C11—N4 | −92.3 (3) |
N3i—Cu1—N3—C17 | 52.10 (16) | N4—C12—C13—C14 | 180.0 (3) |
N1—Cu1—N3—C17 | 157.37 (17) | C17—C12—C13—C14 | −0.1 (4) |
N1i—Cu1—N3—C17 | −56.28 (18) | C12—C13—C14—C15 | −0.5 (5) |
C7—N1—C1—C6 | −0.3 (2) | C13—C14—C15—C16 | 0.0 (5) |
Cu1—N1—C1—C6 | 169.84 (15) | C14—C15—C16—C17 | 1.1 (4) |
C7—N1—C1—C2 | 176.9 (2) | N4—C12—C17—C16 | −178.9 (2) |
Cu1—N1—C1—C2 | −13.0 (3) | C13—C12—C17—C16 | 1.2 (4) |
C6—C1—C2—C3 | −1.5 (3) | N4—C12—C17—N3 | 0.3 (3) |
N1—C1—C2—C3 | −178.5 (2) | C13—C12—C17—N3 | −179.7 (2) |
C1—C2—C3—C4 | 1.2 (4) | C15—C16—C17—C12 | −1.6 (4) |
C2—C3—C4—C5 | −0.1 (4) | C15—C16—C17—N3 | 179.4 (3) |
C3—C4—C5—C6 | −0.7 (4) | C11—N3—C17—C12 | −0.4 (3) |
C4—C5—C6—N2 | 178.3 (3) | Cu1—N3—C17—C12 | 165.21 (16) |
C4—C5—C6—C1 | 0.3 (4) | C11—N3—C17—C16 | 178.7 (3) |
C2—C1—C6—N2 | −177.6 (2) | Cu1—N3—C17—C16 | −15.7 (4) |
N1—C1—C6—N2 | 0.0 (3) | N1—C7—N2—C6 | −0.6 (3) |
C2—C1—C6—C5 | 0.8 (4) | C8—C7—N2—C6 | 176.1 (2) |
N1—C1—C6—C5 | 178.4 (2) | C5—C6—N2—C7 | −177.8 (3) |
C1—N1—C7—N2 | 0.6 (3) | C1—C6—N2—C7 | 0.4 (3) |
Cu1—N1—C7—N2 | −168.34 (16) | N3—C11—N4—C12 | −0.1 (3) |
C1—N1—C7—C8 | −175.9 (2) | C10—C11—N4—C12 | 175.4 (2) |
Cu1—N1—C7—C8 | 15.1 (4) | C13—C12—N4—C11 | 179.8 (3) |
N1—C7—C8—C9 | 83.1 (3) | C17—C12—N4—C11 | −0.1 (3) |
Symmetry code: (i) −x+1/2, −y+3/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O2ii | 0.82 (1) | 2.01 (2) | 2.814 (4) | 167 (5) |
O4—H4A···O1ii | 0.82 (1) | 2.60 (4) | 3.261 (5) | 139 (5) |
N2—H2N···O3iii | 0.78 (3) | 2.21 (3) | 2.929 (4) | 152 (3) |
N2—H2N···O2iii | 0.78 (3) | 2.37 (3) | 2.969 (3) | 134 (3) |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C17H16N4)2](NO3)2·2C2H6O |
Mr | 804.32 |
Crystal system, space group | Orthorhombic, Pccn |
Temperature (K) | 297 |
a, b, c (Å) | 14.4793 (10), 17.8978 (13), 14.3078 (10) |
V (Å3) | 3707.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.66 |
Crystal size (mm) | 0.45 × 0.32 × 0.20 |
Data collection | |
Diffractometer | Bruker APEX CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23966, 4453, 3394 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.130, 1.07 |
No. of reflections | 4453 |
No. of parameters | 261 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.48, −0.25 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.
N3—Cu1—N3i | 144.46 (12) | N3—Cu1—N1i | 90.25 (7) |
N3—Cu1—N1 | 100.35 (7) | N1—Cu1—N1i | 144.89 (11) |
Symmetry code: (i) −x+1/2, −y+3/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O2ii | 0.816 (10) | 2.014 (17) | 2.814 (4) | 167 (5) |
O4—H4A···O1ii | 0.816 (10) | 2.60 (4) | 3.261 (5) | 139 (5) |
N2—H2N···O3iii | 0.78 (3) | 2.21 (3) | 2.929 (4) | 152 (3) |
N2—H2N···O2iii | 0.78 (3) | 2.37 (3) | 2.969 (3) | 134 (3) |
Symmetry codes: (ii) −x+1, y−1/2, −z+1/2; (iii) x−1, y, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Interest in bis(2-benzimidazolyl)alkanes is widespread, due to their wide-ranging antiviral activity (Roderick et al., 1972). Herein, we report the crystal structure of the title compound (I). In the cation (Fig. 1), the CuII ion lies on a crystallogrphic twofold axis. Hence, the CuII ion is coordinated by four N atoms (N1, N3, N1a, N3a [symmety code: (a) 1/2 - x, 3/2 - y, z]) from two dbz ligangs. The bond anlges listed in Table 1 indicate a distorted square-planar coordination geomtry.
In the crystal structure, molecules are linked by N—Hbenzimidazole···Onitrate and O—Hmethanol···O nitrate hydrogen bonds, forming a two-dimensional framework structure perpendicular to the ab plane (Table 2, Fig. 2).