Acta Cryst.(2004). E60, m277±m278 DOI: 10.1107/S1600536804002053 Wuet al [Cu(C24H21N7)(H2O)](ClO4)2C6H7NOH2O
m277
metal-organic papers
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Aqua[tris(1
H
-benzimidazol-2-ylmethyl)-amine]copper(II) diperchlorate 4-picoline
N
-oxide monohydrate
Huilu Wu,a* Yizhi Liband
Yici Gaoa
aDepartment of Chemistry, Lanzhou University,
Lanzhou 730000, People's Republic of China, andbCoordination Chemistry Institute, State Key
Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 293 K
Mean(C±C) = 0.007 AÊ Disorder in solvent or counterion
Rfactor = 0.054
wRfactor = 0.171
Data-to-parameter ratio = 14.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
In the title compound, [Cu(C24H21N7)(H2O)](ClO4)2
-C6H7NOH2O, the copper ion is bonded to a tris(1H
-benzimidazol-2-ylmethyl)amine (ntb) and a water molecule, resulting in it being ®ve-coordinate with an N4O ligand set.
The coordination geometry of the copper ion may best be described as distorted trigonal bipyramidal, withC3 molecular symmetry.
Comment
The asymmetric unit of the title compound, (I) (Fig. 1), consists of a discrete [Cu(ntb)(H2O)]2+cation [ntb is tris(1H
-benzimidazol-2-ylmethyl)amine], two perchlorate anions, a molecule of 4-picoline N-oxide and one molecule of water of crystallization. The water molecule is disordered over two sites with equal occupancies. The copper ion is ®ve-coordinate with
an N4O ligand set. The ntb ligand acts as a tetradentate
N-atom donor, and an aqua O atom completes the coordin-ation. The coordination geometry of the copper may best be described as distorted trigonal bipyramidal, with approximate
site symmetry C3. This geometry is assumed by the copper
center to relieve the steric crowding. The trigonal plane is occupied by the three ligating N atoms of the benzimidazolyl groups. The Cu atom protrudes towards atom O1 and is 0.294 AÊ out of the plane. The axial ligating atoms are N1 and O1, with CuÐN1 = 2.096 (3) AÊ, CuÐO1 = 1.959 (3) AÊ and
N1ÐCu1ÐO1 = 178.71 (11). The three benzimidazole ring
arms of the ntb ligand form a cone-shaped cavity. The bond lengths and angles are normal. In the crystal structure, there
are weak CÐH O and strong NÐH O and OÐH O
hydrogen bonds (Table 1 and Fig. 2).
Experimental
To a stirred solution of tris(1H-benzimidazol-2-ylmethyl)amine (407 mg, 1 mmol) in methanol (20 ml) was added Cu(ClO4)26H2O
(370 mg, 1 mmol), followed by a solution of 4-picoline N-oxide (109 mg, 1 mmol) in methanol (5 ml). The resulting clear blue solu-tion was stirred for 8 h and then allowed to stand at room tempera-ture. Blue±green crystals suitable for X-ray diffraction studies were obtained after two weeks (367 mg, yield 45%). Found: C 43.82, H 3.99, N 13.93%; calculated for C30H32Cl2CuN8O11: C 44.21, H 3.96, N
13.75%.
Crystal data [Cu(C24H21N7)(H2
O)]-(ClO4)2C6H7NOH2O Mr= 815.08
Triclinic,P1
a= 11.6048 (13) AÊ
b= 13.8916 (15) AÊ
c= 14.3273 (16) AÊ
= 62.430 (2) = 89.898 (2) = 66.140 (2) V= 1822.8 (4) AÊ3
Z= 2
Dx= 1.485 Mg mÿ3
MoKradiation Cell parameters from 2688
re¯ections
= 2.3±23.1 = 0.81 mmÿ1 T= 293 (2) K Cuboid, blue±green 0.30.20.2 mm
Data collection Bruker SMART CCD
diffractometer
'and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin= 0.82,Tmax= 0.85
9837 measured re¯ections
6971 independent re¯ections 4936 re¯ections withI> 2(I)
Rint= 0.026
max= 26.0 h=ÿ14!13
k=ÿ17!11
l=ÿ17!12 Re®nement
Re®nement onF2 R[F2> 2(F2)] = 0.054 wR(F2) = 0.171 S= 1.07 6971 re¯ections 485 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.1057P)2
+ 0.3685P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.31 e AÊÿ3 min=ÿ0.33 e AÊÿ3
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
N2ÐH2A O1W 0.86 2.01 2.844 (6) 163 N4ÐH4A O2 0.86 1.96 2.728 (4) 147 N4ÐH4A O23i 0.86 2.48 2.935 (4) 114
N6ÐH6A O13 0.86 2.16 3.015 (4) 170 N6ÐH6A O12 0.86 2.49 3.148 (4) 134 O1ÐH1C O2ii 0.81 (3) 1.81 (3) 2.620 (4) 177 (5)
O1ÐH1D O12iii 0.81 (3) 2.07 (3) 2.852 (4) 162 (4)
O1WÐH1WB O21 0.85 1.98 2.830 (6) 180 O1WÐH1WA O2Wiv 0.85 2.48 3.288 (8) 158
C14ÐH14 O11v 0.93 2.52 3.259 (5) 136
Symmetry codes: (i) 2ÿx;ÿy;1ÿz; (ii) 1ÿx;1ÿy;1ÿz; (iii) 1ÿx;ÿy;1ÿz; (iv)
x;1y;zÿ1; (v)xÿ1;1y;z.
H atoms bonded to the coordinated water molecule were included in the re®nement with both OÐH distances restrained to be equal. All other H atoms were placed in calculated positions, with CÐH distances ranging from 0.93 to 1.00 AÊ, NÐH = 0.86 AÊ and OÐH = 0.85 AÊ, and treated as riding, withUiso= 1.2Ueq(1.5Ueqfor methyl H
atoms) of the carrier atom. .
Data collection:SMART(Bruker, 2000); cell re®nement:SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 1996); program(s) used to re®ne structure: SHELXTL; molecular graphics: PLATON(Spek, 2004) andSHELXTL; software used to prepare material for publication: SHELXTL.
References
Bruker (2000).SMART,SAINTandSADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996).SHELXTL.Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spek, A. L. (2004).PLATON.University of Utrecht, The Netherlands.
Figure 1
View of the asymmetric unit of the title compound. Displacement ellipsoids are at the 30% probability level and H atoms bonded to C atoms are not shown
Figure 2
supporting information
sup-1
Acta Cryst. (2004). E60, m277–m278
supporting information
Acta Cryst. (2004). E60, m277–m278 [https://doi.org/10.1107/S1600536804002053]
Aqua[tris(1
H
-benzimidazol-2-ylmethyl)amine]copper(II) diperchlorate
4-picoline
N
-oxide monohydrate
Huilu Wu, Yizhi Li and Yici Gao
Aqua[tris(1H-benzimidazol-2-ylmethyl)amine]copper(II) diperchlorate 4-picoline N-oxide monohydrate
Crystal data
[Cu(C24H21N7)(H2O)](ClO4)2·C6H7NO·H2O
Mr = 815.08
Triclinic, P1 Hall symbol: -P 1
a = 11.6048 (13) Å
b = 13.8916 (15) Å
c = 14.3273 (16) Å
α = 62.430 (2)°
β = 89.898 (2)°
γ = 66.140 (2)°
V = 1822.8 (4) Å3
Z = 2
F(000) = 838
Dx = 1.485 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2688 reflections
θ = 2.3–23.1°
µ = 0.81 mm−1
T = 293 K
Cuboid, blue-green 0.3 × 0.2 × 0.2 mm
Data collection
Bruker SMART CCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin = 0.82, Tmax = 0.85
9837 measured reflections 6971 independent reflections 4936 reflections with I > 2σ(I)
Rint = 0.026
θmax = 26.0°, θmin = 1.9°
h = −14→13
k = −17→11
l = −17→12
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.054
wR(F2) = 0.171
S = 1.07 6971 reflections 485 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.1057P)2 + 0.3685P] where P = (Fo2 + 2Fc2)/3
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 (Å2)
x y z Uiso*/Ueq Occ. (<1)
Cu1 0.50078 (4) 0.34966 (4) 0.34048 (4) 0.04824 (17)
C1 0.7636 (4) 0.2685 (3) 0.3031 (3) 0.0510 (9)
H1A 0.7781 0.2049 0.2865 0.061*
H1B 0.8463 0.2660 0.3192 0.061*
C2 0.6735 (4) 0.3903 (3) 0.2095 (3) 0.0495 (8)
C3 0.5965 (4) 0.5610 (4) 0.0552 (3) 0.0514 (9)
C4 0.5718 (4) 0.6631 (4) −0.0423 (3) 0.0524 (9)
H4 0.6385 0.6738 −0.0749 0.063*
C5 0.4449 (4) 0.7489 (4) −0.0898 (3) 0.0545 (9)
H5 0.4253 0.8184 −0.1565 0.065*
C6 0.3493 (4) 0.7350 (4) −0.0427 (3) 0.0493 (8)
H6 0.2649 0.7963 −0.0769 0.059*
C7 0.3704 (4) 0.6328 (3) 0.0552 (3) 0.0495 (8)
H7 0.3021 0.6238 0.0857 0.059*
C8 0.4964 (4) 0.5453 (3) 0.1053 (3) 0.0492 (8)
C9 0.7385 (4) 0.2975 (4) 0.4601 (3) 0.0486 (8)
H9A 0.8219 0.2379 0.5100 0.058*
H9B 0.7437 0.3721 0.4123 0.058*
C10 0.6371 (4) 0.3211 (3) 0.5199 (3) 0.0487 (8)
C11 0.5289 (4) 0.3407 (3) 0.6404 (3) 0.0491 (8)
C12 0.4912 (4) 0.3410 (3) 0.7314 (3) 0.0485 (8)
H12 0.5489 0.3230 0.7889 0.058*
C13 0.3643 (4) 0.3692 (3) 0.7325 (3) 0.0506 (9)
H13 0.3357 0.3669 0.7938 0.061*
C14 0.2765 (4) 0.4011 (3) 0.6454 (3) 0.0517 (9)
H14 0.1900 0.4227 0.6478 0.062*
C15 0.3177 (4) 0.4009 (3) 0.5541 (3) 0.0481 (8)
H15 0.2592 0.4224 0.4953 0.058*
C16 0.4456 (4) 0.3685 (3) 0.5524 (3) 0.0508 (9)
C17 0.7363 (4) 0.1203 (3) 0.4671 (3) 0.0497 (9)
H17A 0.7289 0.1028 0.5401 0.060*
H17B 0.8245 0.0693 0.4695 0.060*
C18 0.6443 (4) 0.0969 (3) 0.4202 (3) 0.0484 (8)
C19 0.5604 (4) 0.0028 (3) 0.3768 (3) 0.0520 (9)
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Acta Cryst. (2004). E60, m277–m278
H20 0.5942 −0.1547 0.3838 0.064*
C21 0.4122 (4) −0.0298 (4) 0.3005 (3) 0.0531 (9)
H21 0.3917 −0.0804 0.2858 0.064*
C22 0.3192 (4) 0.0894 (4) 0.2630 (3) 0.0504 (9)
H22 0.2375 0.1163 0.2246 0.060*
C23 0.3444 (4) 0.1683 (3) 0.2809 (3) 0.0489 (8)
H23 0.2821 0.2481 0.2558 0.059*
C24 0.4676 (4) 0.1232 (3) 0.3385 (3) 0.0480 (8)
N1 0.7024 (3) 0.2504 (3) 0.3965 (3) 0.0476 (7)
N2 0.7076 (3) 0.4596 (3) 0.1247 (3) 0.0485 (7)
H2A 0.7851 0.4435 0.1155 0.058*
N3 0.5506 (3) 0.4380 (3) 0.2032 (3) 0.0497 (7)
N4 0.6504 (3) 0.3132 (3) 0.6147 (3) 0.0488 (7)
H4A 0.7205 0.2947 0.6536 0.059*
N5 0.5154 (3) 0.3546 (3) 0.4786 (3) 0.0490 (7)
N6 0.6696 (3) −0.0113 (3) 0.4293 (3) 0.0498 (7)
H6A 0.7415 −0.0772 0.4621 0.060*
N7 0.5253 (3) 0.1800 (3) 0.3674 (3) 0.0493 (7)
O1 0.3126 (3) 0.4458 (2) 0.2873 (2) 0.0487 (6)
H1C 0.279 (4) 0.513 (3) 0.280 (4) 0.058*
H1D 0.266 (4) 0.418 (4) 0.320 (3) 0.058*
C25 0.9607 (4) 0.1920 (4) 0.8957 (3) 0.0532 (9)
H25A 0.8965 0.1920 0.9346 0.064*
C26 1.0882 (4) 0.1155 (4) 0.9495 (3) 0.0543 (9)
H26A 1.1082 0.0629 1.0238 0.065*
C27 1.1840 (4) 0.1149 (4) 0.8981 (3) 0.0526 (9)
C28 1.1477 (4) 0.1899 (4) 0.7901 (3) 0.0533 (9)
H28A 1.2114 0.1925 0.7508 0.064*
C29 1.0202 (4) 0.2625 (4) 0.7358 (3) 0.0534 (9)
H29A 0.9981 0.3103 0.6607 0.064*
C30 1.3312 (4) 0.0401 (4) 0.9505 (3) 0.0528 (9)
H30A 1.3510 −0.0429 1.0015 0.079*
H30B 1.3548 0.0746 0.9871 0.079*
H30C 1.3788 0.0422 0.8953 0.079*
N8 0.9282 (3) 0.2639 (3) 0.7918 (3) 0.0507 (7)
O2 0.8054 (3) 0.3350 (2) 0.7388 (2) 0.0507 (6)
Cl1 0.93211 (9) −0.33414 (9) 0.58944 (8) 0.0520 (2)
O11 0.9749 (3) −0.3961 (3) 0.5335 (2) 0.0565 (7)
O12 0.7999 (3) −0.2967 (2) 0.5804 (2) 0.0545 (6)
O13 0.9352 (3) −0.2232 (2) 0.5465 (2) 0.0565 (7)
O14 0.9982 (3) −0.4192 (2) 0.6935 (2) 0.0558 (7)
Cl2 1.00301 (9) 0.01759 (8) 0.25849 (8) 0.0516 (2)
O21 0.9869 (3) 0.1253 (2) 0.1735 (2) 0.0568 (7)
O22 0.8882 (3) 0.0115 (2) 0.2578 (2) 0.0558 (7)
O23 1.1131 (3) −0.0801 (2) 0.2731 (2) 0.0572 (7)
O24 1.0190 (3) 0.0226 (3) 0.3470 (2) 0.0576 (7)
O1W 0.9644 (5) 0.3613 (5) 0.0978 (4) 0.0526 (12) 0.50
H1WA 0.9527 0.3981 0.0293 0.063* 0.50
O2W 0.9988 (6) −0.4987 (5) 0.8495 (5) 0.0586 (14) 0.50
H2WC 0.9400 −0.5168 0.8761 0.070* 0.50
H2WD 1.0716 −0.5620 0.8782 0.070* 0.50
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Cu1 0.0465 (3) 0.0480 (3) 0.0494 (3) −0.0213 (2) 0.0101 (2) −0.0241 (2)
C1 0.048 (2) 0.049 (2) 0.058 (2) −0.0229 (16) 0.0080 (17) −0.0272 (19)
C2 0.053 (2) 0.0471 (19) 0.046 (2) −0.0234 (17) 0.0112 (17) −0.0210 (17)
C3 0.056 (2) 0.052 (2) 0.052 (2) −0.0270 (18) 0.0150 (18) −0.0291 (19)
C4 0.052 (2) 0.054 (2) 0.050 (2) −0.0250 (17) 0.0110 (17) −0.0243 (19)
C5 0.058 (2) 0.047 (2) 0.051 (2) −0.0213 (17) 0.0116 (18) −0.0203 (18)
C6 0.049 (2) 0.052 (2) 0.046 (2) −0.0213 (17) 0.0076 (16) −0.0251 (18)
C7 0.052 (2) 0.049 (2) 0.047 (2) −0.0225 (17) 0.0092 (16) −0.0246 (17)
C8 0.048 (2) 0.051 (2) 0.051 (2) −0.0234 (16) 0.0119 (16) −0.0261 (18)
C9 0.0464 (19) 0.0476 (19) 0.050 (2) −0.0202 (16) 0.0109 (16) −0.0241 (17)
C10 0.048 (2) 0.050 (2) 0.050 (2) −0.0241 (16) 0.0107 (16) −0.0245 (18)
C11 0.051 (2) 0.048 (2) 0.048 (2) −0.0205 (17) 0.0107 (17) −0.0262 (18)
C12 0.052 (2) 0.050 (2) 0.046 (2) −0.0236 (17) 0.0093 (16) −0.0262 (18)
C13 0.052 (2) 0.051 (2) 0.054 (2) −0.0242 (17) 0.0115 (17) −0.0296 (19)
C14 0.051 (2) 0.046 (2) 0.055 (2) −0.0190 (17) 0.0136 (18) −0.0251 (18)
C15 0.050 (2) 0.0456 (19) 0.047 (2) −0.0215 (16) 0.0102 (16) −0.0229 (17)
C16 0.054 (2) 0.0452 (19) 0.050 (2) −0.0213 (17) 0.0107 (18) −0.0227 (17)
C17 0.048 (2) 0.0444 (19) 0.051 (2) −0.0190 (16) 0.0121 (17) −0.0219 (17)
C18 0.048 (2) 0.0434 (19) 0.049 (2) −0.0189 (16) 0.0098 (16) −0.0209 (17)
C19 0.056 (2) 0.048 (2) 0.053 (2) −0.0232 (17) 0.0140 (18) −0.0270 (19)
C20 0.058 (2) 0.047 (2) 0.053 (2) −0.0249 (18) 0.0145 (18) −0.0234 (19)
C21 0.055 (2) 0.052 (2) 0.054 (2) −0.0239 (18) 0.0141 (18) −0.0288 (19)
C22 0.049 (2) 0.055 (2) 0.051 (2) −0.0258 (17) 0.0141 (17) −0.0282 (18)
C23 0.054 (2) 0.0454 (19) 0.050 (2) −0.0228 (16) 0.0132 (17) −0.0252 (17)
C24 0.048 (2) 0.0465 (19) 0.051 (2) −0.0206 (16) 0.0141 (17) −0.0262 (18)
N1 0.0454 (16) 0.0447 (16) 0.0486 (17) −0.0189 (13) 0.0103 (13) −0.0221 (14)
N2 0.0463 (17) 0.0521 (17) 0.0520 (18) −0.0233 (14) 0.0127 (14) −0.0292 (15)
N3 0.0520 (18) 0.0479 (17) 0.0489 (17) −0.0240 (14) 0.0127 (14) −0.0233 (15)
N4 0.0468 (17) 0.0491 (17) 0.0542 (19) −0.0223 (14) 0.0090 (14) −0.0284 (16)
N5 0.0484 (17) 0.0518 (17) 0.0484 (17) −0.0232 (14) 0.0097 (14) −0.0260 (15)
N6 0.0511 (18) 0.0463 (16) 0.0544 (19) −0.0229 (14) 0.0119 (15) −0.0265 (15)
N7 0.0496 (17) 0.0492 (17) 0.0492 (17) −0.0231 (14) 0.0101 (14) −0.0244 (15)
O1 0.0497 (15) 0.0485 (14) 0.0486 (15) −0.0223 (12) 0.0124 (12) −0.0251 (13)
C25 0.053 (2) 0.056 (2) 0.052 (2) −0.0234 (18) 0.0105 (18) −0.028 (2)
C26 0.053 (2) 0.054 (2) 0.049 (2) −0.0198 (18) 0.0103 (17) −0.0246 (19)
C27 0.048 (2) 0.052 (2) 0.053 (2) −0.0218 (17) 0.0089 (17) −0.0240 (19)
C28 0.054 (2) 0.051 (2) 0.059 (2) −0.0260 (18) 0.0152 (18) −0.029 (2)
C29 0.055 (2) 0.056 (2) 0.051 (2) −0.0273 (18) 0.0137 (18) −0.0257 (19)
C30 0.052 (2) 0.052 (2) 0.051 (2) −0.0220 (17) 0.0105 (17) −0.0244 (18)
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Acta Cryst. (2004). E60, m277–m278
O2 0.0510 (15) 0.0479 (14) 0.0501 (14) −0.0211 (12) 0.0059 (12) −0.0236 (12)
Cl1 0.0501 (5) 0.0527 (5) 0.0541 (5) −0.0238 (4) 0.0124 (4) −0.0273 (5)
O11 0.0577 (16) 0.0565 (16) 0.0567 (16) −0.0264 (13) 0.0144 (13) −0.0293 (14)
O12 0.0516 (15) 0.0542 (15) 0.0548 (16) −0.0236 (12) 0.0118 (12) −0.0259 (13)
O13 0.0574 (16) 0.0521 (15) 0.0574 (17) −0.0228 (13) 0.0135 (13) −0.0277 (14)
O14 0.0541 (15) 0.0539 (15) 0.0532 (16) −0.0217 (13) 0.0099 (13) −0.0250 (14)
Cl2 0.0502 (5) 0.0504 (5) 0.0528 (5) −0.0208 (4) 0.0107 (4) −0.0267 (4)
O21 0.0580 (16) 0.0551 (15) 0.0555 (16) −0.0271 (13) 0.0148 (13) −0.0254 (14)
O22 0.0553 (16) 0.0536 (15) 0.0559 (16) −0.0248 (13) 0.0109 (13) −0.0257 (13)
O23 0.0571 (16) 0.0496 (15) 0.0587 (17) −0.0203 (13) 0.0132 (13) −0.0263 (14)
O24 0.0578 (16) 0.0576 (16) 0.0533 (16) −0.0241 (13) 0.0135 (13) −0.0267 (14)
O1W 0.056 (3) 0.050 (3) 0.049 (3) −0.025 (2) 0.015 (2) −0.023 (3)
O2W 0.059 (3) 0.055 (3) 0.057 (3) −0.023 (3) 0.017 (3) −0.028 (3)
Geometric parameters (Å, º)
Cu1—O1 1.959 (3) C18—N6 1.350 (5)
Cu1—N3 2.011 (3) C19—C20 1.369 (5)
Cu1—N5 2.021 (3) C19—N6 1.370 (5)
Cu1—N1 2.096 (3) C19—C24 1.397 (5)
Cu1—N7 2.098 (3) C20—C21 1.360 (6)
C1—N1 1.480 (5) C20—H20 0.9300
C1—C2 1.493 (5) C21—C22 1.389 (5)
C1—H1A 0.9700 C21—H21 0.9300
C1—H1B 0.9700 C22—C23 1.370 (5)
C2—N3 1.289 (5) C22—H22 0.9300
C2—N2 1.335 (5) C23—C24 1.384 (5)
C3—N2 1.370 (5) C23—H23 0.9300
C3—C4 1.373 (5) C24—N7 1.405 (5)
C3—C8 1.404 (5) N2—H2A 0.8600
C4—C5 1.373 (6) N4—H4A 0.8600
C4—H4 0.9300 N6—H6A 0.8600
C5—C6 1.333 (6) O1—H1C 0.81 (3)
C5—H5 0.9300 O1—H1D 0.81 (3)
C6—C7 1.385 (5) C25—N8 1.295 (5)
C6—H6 0.9300 C25—C26 1.373 (6)
C7—C8 1.374 (5) C25—H25A 0.9300
C7—H7 0.9300 C26—C27 1.332 (6)
C8—N3 1.376 (5) C26—H26A 0.9300
C9—C10 1.473 (5) C27—C28 1.347 (6)
C9—N1 1.486 (5) C27—C30 1.552 (5)
C9—H9A 0.9700 C28—C29 1.372 (6)
C9—H9B 0.9700 C28—H28A 0.9300
C10—N4 1.314 (5) C29—N8 1.334 (5)
C10—N5 1.334 (5) C29—H29A 0.9300
C11—C12 1.376 (5) C30—H30A 0.9600
C11—C16 1.388 (5) C30—H30B 0.9600
C12—C13 1.365 (5) N8—O2 1.324 (4)
C12—H12 0.9300 Cl1—O14 1.360 (3)
C13—C14 1.385 (6) Cl1—O11 1.386 (3)
C13—H13 0.9300 Cl1—O13 1.386 (3)
C14—C15 1.392 (6) Cl1—O12 1.391 (3)
C14—H14 0.9300 Cl2—O24 1.320 (3)
C15—C16 1.370 (5) Cl2—O21 1.358 (3)
C15—H15 0.9300 Cl2—O23 1.361 (3)
C16—N5 1.368 (5) Cl2—O22 1.370 (3)
C17—N1 1.476 (5) O1W—H1WB 0.8498
C17—C18 1.478 (5) O1W—H1WA 0.8500
C17—H17A 0.9700 O2W—H2WC 0.8502
C17—H17B 0.9700 O2W—H2WD 0.8500
C18—N7 1.311 (5)
O1—Cu1—N3 97.85 (12) C19—C20—H20 121.1
O1—Cu1—N5 98.21 (12) C20—C21—C22 121.6 (4)
N3—Cu1—N5 128.80 (13) C20—C21—H21 119.2
O1—Cu1—N1 178.71 (11) C22—C21—H21 119.2
N3—Cu1—N1 81.49 (13) C23—C22—C21 121.8 (4)
N5—Cu1—N1 81.40 (13) C23—C22—H22 119.1
O1—Cu1—N7 100.65 (12) C21—C22—H22 119.1
N3—Cu1—N7 111.30 (13) C22—C23—C24 116.6 (4)
N5—Cu1—N7 112.87 (13) C22—C23—H23 121.7
N1—Cu1—N7 80.62 (12) C24—C23—H23 121.7
N1—C1—C2 107.2 (3) C23—C24—C19 121.4 (4)
N1—C1—H1A 110.3 C23—C24—N7 130.9 (3)
C2—C1—H1A 110.3 C19—C24—N7 107.8 (3)
N1—C1—H1B 110.3 C17—N1—C1 110.7 (3)
C2—C1—H1B 110.3 C17—N1—C9 110.1 (3)
H1A—C1—H1B 108.5 C1—N1—C9 112.1 (3)
N3—C2—N2 113.2 (3) C17—N1—Cu1 108.5 (2)
N3—C2—C1 121.2 (3) C1—N1—Cu1 109.3 (2)
N2—C2—C1 125.6 (3) C9—N1—Cu1 106.0 (2)
N2—C3—C4 133.5 (4) C2—N2—C3 107.3 (3)
N2—C3—C8 105.0 (3) C2—N2—H2A 126.3
C4—C3—C8 121.5 (4) C3—N2—H2A 126.3
C3—C4—C5 117.4 (4) C2—N3—C8 106.1 (3)
C3—C4—H4 121.3 C2—N3—Cu1 113.6 (3)
C5—C4—H4 121.3 C8—N3—Cu1 139.6 (3)
C6—C5—C4 121.6 (4) C10—N4—C11 107.2 (3)
C6—C5—H5 119.2 C10—N4—H4A 126.4
C4—C5—H5 119.2 C11—N4—H4A 126.4
C5—C6—C7 122.7 (4) C10—N5—C16 106.5 (3)
C5—C6—H6 118.7 C10—N5—Cu1 111.4 (3)
C7—C6—H6 118.7 C16—N5—Cu1 141.6 (3)
C8—C7—C6 117.3 (4) C18—N6—C19 107.7 (3)
supporting information
sup-7
Acta Cryst. (2004). E60, m277–m278
C6—C7—H7 121.3 C19—N6—H6A 126.1
C7—C8—N3 132.1 (4) C18—N7—C24 106.1 (3)
C7—C8—C3 119.5 (4) C18—N7—Cu1 109.7 (2)
N3—C8—C3 108.3 (3) C24—N7—Cu1 143.4 (3)
C10—C9—N1 107.1 (3) Cu1—O1—H1C 118 (3)
C10—C9—H9A 110.3 Cu1—O1—H1D 119 (3)
N1—C9—H9A 110.3 H1C—O1—H1D 100 (5)
C10—C9—H9B 110.3 N8—C25—C26 121.3 (4)
N1—C9—H9B 110.3 N8—C25—H25A 119.4
H9A—C9—H9B 108.5 C26—C25—H25A 119.4
N4—C10—N5 112.2 (3) C27—C26—C25 121.7 (4)
N4—C10—C9 127.5 (3) C27—C26—H26A 119.2
N5—C10—C9 120.3 (4) C25—C26—H26A 119.2
C12—C11—C16 123.7 (4) C26—C27—C28 115.9 (4)
C12—C11—N4 130.7 (4) C26—C27—C30 126.6 (4)
C16—C11—N4 105.6 (3) C28—C27—C30 117.5 (4)
C13—C12—C11 116.2 (4) C27—C28—C29 122.4 (4)
C13—C12—H12 121.9 C27—C28—H28A 118.8
C11—C12—H12 121.9 C29—C28—H28A 118.8
C12—C13—C14 122.3 (4) N8—C29—C28 119.3 (4)
C12—C13—H13 118.9 N8—C29—H29A 120.4
C14—C13—H13 118.9 C28—C29—H29A 120.4
C13—C14—C15 120.1 (4) C27—C30—H30A 109.5
C13—C14—H14 120.0 C27—C30—H30B 109.5
C15—C14—H14 120.0 H30A—C30—H30B 109.5
C16—C15—C14 118.9 (4) C27—C30—H30C 109.5
C16—C15—H15 120.5 H30A—C30—H30C 109.5
C14—C15—H15 120.5 H30B—C30—H30C 109.5
N5—C16—C15 132.8 (4) C25—N8—O2 121.7 (3)
N5—C16—C11 108.4 (3) C25—N8—C29 119.4 (3)
C15—C16—C11 118.8 (4) O2—N8—C29 118.8 (3)
N1—C17—C18 106.6 (3) O14—Cl1—O11 104.05 (18)
N1—C17—H17A 110.4 O14—Cl1—O13 116.85 (18)
C18—C17—H17A 110.4 O11—Cl1—O13 116.09 (18)
N1—C17—H17B 110.4 O14—Cl1—O12 110.56 (17)
C18—C17—H17B 110.4 O11—Cl1—O12 108.32 (18)
H17A—C17—H17B 108.6 O13—Cl1—O12 100.81 (17)
N7—C18—N6 112.2 (3) O24—Cl2—O21 107.14 (18)
N7—C18—C17 122.8 (3) O24—Cl2—O23 104.35 (19)
N6—C18—C17 125.0 (3) O21—Cl2—O23 113.65 (18)
C20—C19—N6 132.8 (4) O24—Cl2—O22 101.63 (19)
C20—C19—C24 121.0 (4) O21—Cl2—O22 109.53 (18)
N6—C19—C24 106.2 (3) O23—Cl2—O22 119.01 (18)
C21—C20—C19 117.7 (4) H1WB—O1W—H1WA 109.5
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N2—H2A···O1W 0.86 2.01 2.844 (6) 163
N4—H4A···O2 0.86 1.96 2.728 (4) 147
N4—H4A···O23i 0.86 2.48 2.935 (4) 114
N6—H6A···O13 0.86 2.16 3.015 (4) 170
N6—H6A···O12 0.86 2.49 3.148 (4) 134
O1—H1C···O2ii 0.81 (3) 1.81 (3) 2.620 (4) 177 (5)
O1—H1D···O12iii 0.81 (3) 2.07 (3) 2.852 (4) 162 (4)
O1W—H1WB···O21 0.85 1.98 2.830 (6) 180
O1W—H1WA···O2Wiv 0.85 2.48 3.288 (8) 158
C14—H14···O11v 0.93 2.52 3.259 (5) 136
