trans-Bis­[2-(amino­methyl)-1H-benzimidazole-κ²N²,N³]aqua­copper(II) dichloride dihydrate

In the title compound, [Cu(C₈H₉N₃)₂(H₂O)]Cl₂·2H₂O, the Cu^II ion is coordinated in a square-pyramidal geometry, with four N atoms as basal ligands and one water O atom as an apical ligand. The complex mol­ecule is situated on a crystallographic twofold rotation axis. The mol­ecules are bonded to their neighbours by N—H...O, O—H...Cl and N—H...Cl hydogen bonds. The packing is further stabilized by π–π inter­actions between the substituted imidazole mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.101
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1C    ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL-NT (Bruker, 2000); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: PLATON (Spek, 2003).

trans-N,N'-bis[2-(aminomethyl-κN)benzimidazole-κN³)] aquacopper(II) dichloride dihydrate

Crystal data

[Cu(C8H9N3)2(H2O)]Cl2·2H2O	F(000) = 996
Mr = 482.85	Dx = 1.541 Mg m^−3
Monoclinic, C2/c	Melting point = 451.2–455.2 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.765 (4) Å	Cell parameters from 150 reflections
b = 6.7233 (13) Å	θ = 2.3–25.5°
c = 19.074 (4) Å	µ = 1.34 mm^−1
β = 114.03 (3)°	T = 292 K
V = 2080.7 (9) Å^3	Prism, blue
Z = 4	0.34 × 0.27 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1929 independent reflections
Radiation source: fine-focus sealed tube	1384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 8.3 pixels mm^-1	θmax = 25.5°, θmin = 2.3°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −4→8
Tmin = 0.636, Tmax = 0.841	l = −23→21
5024 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: difference Fourier map
wR(F^2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 2.9635P] where P = (Fo^2 + 2Fc^2)/3
1929 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.29 e Å^−3
4 restraints	Δρmin = −0.35 e Å^−3
32 constraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3512 (2)	0.1538 (7)	0.6063 (2)	0.0540 (11)
H1A	0.3286	0.0387	0.5738	0.081*
H1B	0.3285	0.2726	0.5763	0.081*
C2	0.32940 (19)	0.1472 (5)	0.6736 (2)	0.0388 (8)
C3	0.2575 (2)	0.1440 (5)	0.7436 (2)	0.0392 (9)
C4	0.1972 (2)	0.1435 (6)	0.7719 (2)	0.0485 (10)
H4	0.1415	0.1418	0.7394	0.058*
C5	0.2230 (2)	0.1456 (6)	0.8497 (3)	0.0534 (11)
H5	0.1840	0.1466	0.8707	0.064*
C6	0.3072 (2)	0.1462 (6)	0.8988 (2)	0.0551 (11)
H6	0.3226	0.1477	0.9517	0.066*
C7	0.3672 (2)	0.1447 (6)	0.8708 (2)	0.0493 (10)
H7	0.4228	0.1444	0.9038	0.059*
C8	0.34234 (19)	0.1437 (5)	0.7920 (2)	0.0365 (8)
Cl1	0.53581 (7)	0.6948 (2)	0.90942 (6)	0.0665 (4)
Cu1	0.5000	0.17316 (10)	0.7500	0.0360 (2)
H3	0.2093 (12)	0.144 (5)	0.6272 (10)	0.048 (11)*
H2A	0.4314 (17)	0.674 (9)	0.956 (3)	0.13 (3)*
H2B	0.404 (3)	0.548 (3)	0.9920 (19)	0.061 (15)*
H1E	0.487 (3)	0.565 (7)	0.7086 (15)	0.073 (17)*
N1	0.44192 (16)	0.1545 (5)	0.63484 (16)	0.0458 (8)
H1C	0.4574	0.2581	0.6139	0.069*
H1D	0.4581	0.0424	0.6192	0.069*
N2	0.38593 (15)	0.1457 (4)	0.74468 (16)	0.0364 (7)
N3	0.25251 (16)	0.1441 (5)	0.66974 (18)	0.0424 (8)
O1	0.5000	0.5089 (7)	0.7500	0.0627 (11)
O2	0.39209 (19)	0.6504 (6)	0.96643 (18)	0.0631 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0357 (18)	0.077 (3)	0.043 (2)	0.000 (2)	0.0100 (17)	−0.002 (2)
C2	0.0306 (15)	0.040 (2)	0.042 (2)	−0.0025 (16)	0.0104 (15)	−0.0005 (17)
C3	0.0330 (16)	0.031 (2)	0.052 (2)	−0.0035 (15)	0.0158 (16)	−0.0036 (17)
C4	0.0366 (18)	0.039 (2)	0.074 (3)	−0.0019 (17)	0.027 (2)	−0.003 (2)
C5	0.053 (2)	0.046 (3)	0.081 (3)	0.000 (2)	0.048 (2)	0.005 (2)
C6	0.064 (2)	0.056 (3)	0.058 (3)	0.001 (2)	0.038 (2)	0.002 (2)
C7	0.0412 (18)	0.059 (3)	0.047 (2)	−0.003 (2)	0.0178 (18)	0.002 (2)
C8	0.0325 (15)	0.031 (2)	0.048 (2)	−0.0030 (15)	0.0188 (16)	−0.0011 (17)
Cl1	0.0647 (6)	0.0788 (9)	0.0578 (7)	−0.0041 (6)	0.0269 (6)	0.0116 (6)
Cu1	0.0277 (3)	0.0398 (4)	0.0417 (4)	0.000	0.0152 (3)	0.000
N1	0.0368 (14)	0.058 (2)	0.0432 (18)	0.0045 (16)	0.0174 (14)	0.0026 (16)
N2	0.0300 (13)	0.0404 (18)	0.0414 (16)	−0.0035 (13)	0.0172 (12)	0.0000 (14)
N3	0.0265 (14)	0.0449 (19)	0.0477 (19)	−0.0035 (13)	0.0069 (14)	−0.0056 (16)
O1	0.075 (3)	0.045 (3)	0.075 (4)	0.000	0.038 (3)	0.000
O2	0.0513 (16)	0.074 (2)	0.061 (2)	0.0080 (19)	0.0208 (16)	0.0095 (19)

Geometric parameters (Å, º)

C1—N1	1.477 (4)	C7—C8	1.383 (5)
C1—C2	1.484 (5)	C7—H7	0.9300
C1—H1A	0.9700	C8—N2	1.409 (4)
C1—H1B	0.9700	Cu1—N2	1.996 (2)
C2—N2	1.318 (4)	Cu1—N2^i	1.996 (2)
C2—N3	1.338 (4)	Cu1—N1	2.015 (3)
C3—N3	1.375 (5)	Cu1—N1^i	2.015 (3)
C3—C4	1.383 (5)	Cu1—O1	2.257 (5)
C3—C8	1.411 (4)	N1—H1C	0.90
C4—C5	1.363 (5)	N1—H1D	0.90
C4—H4	0.9300	N3—H3	0.86 (2)
C5—C6	1.404 (6)	O1—H1E	0.82 (2)
C5—H5	0.9300	O2—H2A	0.82 (2)
C6—C7	1.375 (5)	O2—H2B	0.82 (2)
C6—H6	0.9300
N1—C1—C2	108.2 (3)	N2—C8—C3	107.4 (3)
N1—C1—H1A	110.1	N2—Cu1—N2^i	169.40 (17)
C2—C1—H1A	110.1	N2—Cu1—N1	83.12 (12)
N1—C1—H1B	110.1	N2^i—Cu1—N1	96.21 (12)
C2—C1—H1B	110.1	N2—Cu1—N1^i	96.21 (12)
H1A—C1—H1B	108.4	N2^i—Cu1—N1^i	83.12 (12)
N2—C2—N3	112.9 (3)	N1—Cu1—N1^i	172.9 (2)
N2—C2—C1	122.1 (3)	N2—Cu1—O1	95.30 (9)
N3—C2—C1	125.0 (3)	N2^i—Cu1—O1	95.30 (9)
N3—C3—C4	131.6 (3)	N1—Cu1—O1	93.57 (10)
N3—C3—C8	106.1 (3)	N1^i—Cu1—O1	93.57 (10)
C4—C3—C8	122.3 (4)	C1—N1—Cu1	113.5 (2)
C5—C4—C3	117.1 (3)	C1—N1—H1C	108.9
C5—C4—H4	121.5	Cu1—N1—H1C	108.9
C3—C4—H4	121.5	C1—N1—H1D	108.9
C4—C5—C6	121.4 (4)	Cu1—N1—H1D	108.9
C4—C5—H5	119.3	H1C—N1—H1D	107.7
C6—C5—H5	119.3	C2—N2—C8	105.8 (3)
C7—C6—C5	121.6 (4)	C2—N2—Cu1	112.6 (2)
C7—C6—H6	119.2	C8—N2—Cu1	141.3 (2)
C5—C6—H6	119.2	C2—N3—C3	107.8 (3)
C6—C7—C8	117.9 (3)	C2—N3—H3	123 (2)
C6—C7—H7	121.1	C3—N3—H3	129 (2)
C8—C7—H7	121.1	Cu1—O1—H1E	118 (4)
C7—C8—N2	132.9 (3)	H2A—O2—H2B	106 (5)
C7—C8—C3	119.7 (3)
N1—C1—C2—N2	1.0 (6)	N3—C2—N2—Cu1	−175.2 (2)
N1—C1—C2—N3	−179.8 (3)	C1—C2—N2—Cu1	4.2 (5)
N3—C3—C4—C5	−179.3 (4)	C7—C8—N2—C2	−178.8 (4)
C8—C3—C4—C5	0.9 (6)	C3—C8—N2—C2	0.0 (4)
C3—C4—C5—C6	−0.6 (6)	C7—C8—N2—Cu1	−6.8 (7)
C4—C5—C6—C7	0.0 (7)	C3—C8—N2—Cu1	172.0 (3)
C5—C6—C7—C8	0.4 (6)	N2^i—Cu1—N2—C2	−92.7 (2)
C6—C7—C8—N2	178.6 (4)	N1—Cu1—N2—C2	−5.6 (2)
C6—C7—C8—C3	−0.1 (6)	N1^i—Cu1—N2—C2	−178.5 (2)
N3—C3—C8—C7	179.6 (3)	O1—Cu1—N2—C2	87.3 (2)
C4—C3—C8—C7	−0.6 (5)	N2^i—Cu1—N2—C8	95.7 (4)
N3—C3—C8—N2	0.6 (4)	N1—Cu1—N2—C8	−177.3 (4)
C4—C3—C8—N2	−179.6 (3)	N1^i—Cu1—N2—C8	9.9 (4)
C2—C1—N1—Cu1	−5.6 (4)	O1—Cu1—N2—C8	−84.3 (4)
N2—Cu1—N1—C1	6.3 (3)	N2—C2—N3—C3	1.1 (4)
N2^i—Cu1—N1—C1	175.6 (3)	C1—C2—N3—C3	−178.3 (4)
O1—Cu1—N1—C1	−88.6 (3)	C4—C3—N3—C2	179.2 (4)
N3—C2—N2—C8	−0.6 (4)	C8—C3—N3—C2	−1.0 (4)
C1—C2—N2—C8	178.7 (4)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···Cl1^ii	0.90	2.41	3.270 (4)	159
O1—H1E···Cl1^i	0.82 (3)	2.29 (3)	3.105 (2)	172 (4)
O2—H2A···Cl1	0.82 (4)	2.37 (4)	3.170 (4)	170 (6)
O2—H2B···Cl1^iii	0.82 (3)	2.39 (3)	3.188 (4)	165 (3)
N3—H3···O2^iv	0.86 (2)	1.95 (2)	2.813 (5)	177 (2)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y−1, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) −x+1/2, y−1/2, −z+3/2.