Tetra­chlorido-1κCl,2κ2Cl,3κCl-bis[μ-4-undecyl-1,4,7-triaza­cyclo­non-1-yl)acetato]-1κ4N,N′,N′′,O:2κO′;2κO′:3κ4N,N′,N′′,O-tricopper(II) dihydrate

Nagel, L.; Forsyth, C.M.; Martin, L.L.

doi:10.1107/S1600536807034538

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Tetrachlorido-1κCl,2κ²Cl,3κCl-bis[μ-4-undecyl-1,4,7-triazacyclonon-1-yl)acetato]-1κ⁴N,N′,N′′,O:2κO′;2κO′:3κ⁴N,N′,N′′,O-tricopper(II) dihydrate

L. Nagel, C. M. Forsyth and L. L. Martin

In the trinuclear title compound, [Cu₃Cl₄(C₁₇H₃₈N₃O₂)₂]·2H₂O or [Cu(AcC₁₁tacn)Cl·H₂O]₂·CuCl₂ [tacn is 1,4,7-triazacyclononone], two Cu atoms are coordinated by a bifunctionalized 1-acetato-4-undecyl-1,4,7-triazacyclononone (AcC₁₁tacn) macrocycle and are five-coordinate, while the third Cu atom, located on a centre of inversion, bridges these two units between two keto O atoms, with two Cl atoms completing a four-coordinate square-planar geometry. The long C₁₁ tails on the macrocycle create well ordered multilayer packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034538/tk2179sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034538/tk2179Isup2.hkl Contains datablock I

CCDC reference: 657615

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.008 Å
R factor = 0.084
wR factor = 0.142
Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.90(9), Rep     0.90(2) ......       4.50 su-Ra
              O3   -H31     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.90(9), Rep     0.90(2) ......       4.50 su-Ra
              O3   -H31     1.555   1.555

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.80 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT731_ALERT_1_C Bond    Calc     0.90(8), Rep     0.90(2) ......       4.00 su-Ra
              O3   -H32     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.89(5), Rep     0.89(2) ......       2.50 su-Ra
              N3   -H3      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.89(5), Rep     0.89(2) ......       2.50 su-Ra
              N3   -H3      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc    2.37(10), Rep     2.37(3) ......       3.33 su-Ra
              H31  -CL1     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of N1     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          R
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1         (2)       2.17
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu2         (2)       1.97
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   8 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

The title complex, (I), crystallizes in the monoclinic space group (P2₁/c), with the asymmetric unit comprising one half of the molecule [Cu(AcC₁₁tacn)Cl.H₂O]₂.CuCl₂, Fig. 1; the Cu2 atom is located on a crystallographic inversion centre. The three N atoms from the macrocycle coordinate facially to Cu1, which is also bound to a terminal Cl with the fifth coordination site completed by the O atom derived from the N-acetyl group. Two of these units are further connected via the keto-O atoms to a four coordinate copper dichloride entity. The Cu1—Cl1 bond distance (2.2645 (14) Å) is slightly longer than the Cu2—Cl2 distance of 2.2512 (14) Å, but this may also reflect the interaction of Cl1 with the water molecule via a O3—H31···Cl1 (2.37 (3) Å) hydrogen bond. The Cu—N distances are inequivalent with the C₁₁ substituted N atom having the longest bond (Cu1—N2 2.289 (4) Å) whilst the secondary amine has the shortest (Cu1—N3 1.985 (4) Å).

The cell contents, when viewed along the b axis, Fig. 2, show the straight chain C₁₁ units form interdigitated layers which separate the hydrophilic {Cu(Actacn)Cl}.CuCl₂ moieties, the latter associated via intermolecular N3—H3···Cl2ⁱ hydrogen bonds (Table 1).

Related literature top

There are several reports of carboxylate functionalized 1,4,7-triazacyclononane (tacn) (Mondal et al., 2003; Neves et al., 1988; Graham et al., 1997; Studer et al., 1989; Schulz et al., 1996). In contrast, the arrangement of long hydrophobic carbon tails has been underrepresented (Fallis et al., 1998; Battle & Martin, 2006). The title complex combines both groups and results in a trinuclear copper complex. For synthesis, see: Zhang et al. (1995).

Experimental top

The title complex was synthesized using a modification of the published procedure (Zhang et al., 1995). 1-Acetato-4-undecyl-1,4,7-triazacyclononane trihydrochloride (0.1 g, 0.22 mmol) was dissolved in MeOH (5 ml) and mixed with 1 equivalent of CuCl₂.6H₂O (0.038 g, 0.22 mmol) dissolved in MeOH (1 ml). Addition of 1.1 equivalent NaOAc (0.0076 g, 0.2 4 mmol) dissolved in MeOH resulted in a dark-green solution. Slow evaporation of the solution resulted in the deposition of blue-green crystals suitable for X-ray diffraction analysis. The solid was collected by filtration and air-dried (0.04 g, 18%). IR (KBr): 3199, 2920, 1578 (νC—O), 1491, 1466, 1445, 1403, 1313 (νC—O) cm^-1. UV/vis (MeCN): λ_max(ε) 265 (934), 461 (114) nm (L.mol^-1.cm).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; 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: SHELXL97.

Figures top

	Fig. 1. A view of (I) showing atomic labelling and displacement ellipsoids at the 50% probability level.
	Fig. 2. Cell contents as viewed down the b axis. H atoms have been omitted for clarity.

Tetrachlorido-1κCl,2κ²Cl,3κCl- bis[µ-4-undecyl-1,4,7-triazacyclonon-1-yl)acetato]-1κ⁴N,N',N'',O:2κO'; 2κO':3κ⁴N,N',N'',O-tricopper(II) dihydrate top

Crystal data top

[Cu₃Cl₄(C₁₇H₃₈N₃O₂)₂]·2H₂O	F(000) = 1106
M_r = 1049.50	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25491 reflections
a = 22.1182 (11) Å	θ = 2.8–27.5°
b = 7.8330 (4) Å	µ = 1.56 mm⁻¹
c = 14.6177 (7) Å	T = 123 K
β = 104.570 (2)°	Plate, blue-green
V = 2451.1 (2) Å³	0.20 × 0.10 × 0.05 mm
Z = 2

Data collection top

Bruker X8 APEX CCD diffractometer	5625 independent reflections
Radiation source: fine-focus sealed tube	4994 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
φ scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −28→28
T_min = 0.746, T_max = 0.926	k = −10→10
25491 measured reflections	l = −18→18

Refinement top

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.32	w = 1/[σ²(F_o²) + 12.2399P] where P = (F_o² + 2F_c²)/3
5625 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.62 e Å⁻³
3 restraints	Δρ_min = −1.02 e Å⁻³

Crystal data top

[Cu₃Cl₄(C₁₇H₃₈N₃O₂)₂]·2H₂O	V = 2451.1 (2) Å³
M_r = 1049.50	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.1182 (11) Å	µ = 1.56 mm⁻¹
b = 7.8330 (4) Å	T = 123 K
c = 14.6177 (7) Å	0.20 × 0.10 × 0.05 mm
β = 104.570 (2)°

Data collection top

Bruker X8 APEX CCD diffractometer	5625 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4994 reflections with I > 2σ(I)
T_min = 0.746, T_max = 0.926	R_int = 0.071
25491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	3 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.32	w = 1/[σ²(F_o²) + 12.2399P] where P = (F_o² + 2F_c²)/3
5625 reflections	Δρ_max = 0.62 e Å⁻³
271 parameters	Δρ_min = −1.02 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
Cu1	0.61289 (3)	0.74292 (8)	−0.20823 (4)	0.01211 (15)
Cu2	0.5000	0.5000	0.0000	0.0165 (2)
Cl1	0.61753 (6)	1.00100 (16)	−0.13697 (9)	0.0193 (3)
Cl2	0.41046 (7)	0.64527 (17)	−0.05565 (10)	0.0252 (3)
O1	0.56465 (17)	0.6326 (5)	−0.1290 (2)	0.0154 (8)
O2	0.49883 (18)	0.4205 (5)	−0.1271 (3)	0.0189 (8)
O3	0.7218 (3)	1.1587 (10)	0.0423 (4)	0.0563 (16)
N1	0.5975 (2)	0.5189 (5)	−0.2818 (3)	0.0145 (9)
N2	0.7136 (2)	0.6474 (6)	−0.1574 (3)	0.0147 (9)
N3	0.6437 (2)	0.8278 (6)	−0.3163 (3)	0.0167 (9)
C1	0.6565 (2)	0.4132 (6)	−0.2570 (4)	0.0150 (10)
H1A	0.6788	0.4268	−0.3073	0.018*
H1B	0.6451	0.2913	−0.2549	0.018*
C2	0.6998 (3)	0.4626 (6)	−0.1629 (4)	0.0176 (11)
H2A	0.6804	0.4307	−0.1113	0.021*
H2B	0.7394	0.3982	−0.1537	0.021*
C3	0.7453 (3)	0.7104 (7)	−0.2280 (4)	0.0191 (11)
H3A	0.7463	0.6189	−0.2744	0.023*
H3B	0.7889	0.7416	−0.1964	0.023*
C4	0.7115 (3)	0.8647 (7)	−0.2790 (4)	0.0212 (12)
H4A	0.7169	0.9627	−0.2349	0.025*
H4B	0.7298	0.8961	−0.3319	0.025*
C5	0.6297 (3)	0.7046 (7)	−0.3966 (4)	0.0182 (11)
H5A	0.6685	0.6444	−0.4000	0.022*
H5B	0.6137	0.7668	−0.4568	0.022*
C6	0.5813 (3)	0.5755 (7)	−0.3828 (3)	0.0166 (11)
H6A	0.5392	0.6282	−0.3992	0.020*
H6B	0.5807	0.4759	−0.4247	0.020*
C7	0.5455 (2)	0.4318 (7)	−0.2560 (4)	0.0167 (11)
H7A	0.5541	0.3077	−0.2505	0.020*
H7B	0.5068	0.4494	−0.3066	0.020*
C8	0.5361 (2)	0.4972 (7)	−0.1645 (4)	0.0164 (11)
C9	0.7438 (2)	0.7052 (7)	−0.0614 (4)	0.0195 (12)
H9A	0.7154	0.6792	−0.0205	0.023*
H9B	0.7481	0.8309	−0.0628	0.023*
C10	0.8079 (3)	0.6299 (8)	−0.0148 (4)	0.0269 (14)
H10A	0.8035	0.5073	−0.0014	0.032*
H10B	0.8354	0.6397	−0.0585	0.032*
C11	0.8375 (2)	0.7237 (8)	0.0771 (4)	0.0214 (12)
H11A	0.8443	0.8442	0.0618	0.026*
H11B	0.8075	0.7230	0.1172	0.026*
C12	0.8988 (3)	0.6509 (8)	0.1337 (4)	0.0258 (13)
H12A	0.9311	0.6706	0.0987	0.031*
H12B	0.8942	0.5260	0.1398	0.031*
C13	0.9208 (3)	0.7283 (8)	0.2317 (4)	0.0274 (14)
H13A	0.9258	0.8529	0.2251	0.033*
H13B	0.8879	0.7107	0.2658	0.033*
C14	0.9817 (3)	0.6562 (8)	0.2914 (4)	0.0265 (13)
H14A	1.0155	0.6814	0.2600	0.032*
H14B	0.9779	0.5306	0.2947	0.032*
C15	0.9999 (3)	0.7275 (9)	0.3913 (4)	0.0276 (14)
H15A	1.0033	0.8532	0.3877	0.033*
H15B	0.9661	0.7018	0.4225	0.033*
C16	1.0606 (3)	0.6581 (9)	0.4518 (4)	0.0278 (14)
H16A	1.0946	0.6851	0.4211	0.033*
H16B	1.0575	0.5323	0.4549	0.033*
C17	1.0781 (3)	0.7283 (8)	0.5517 (4)	0.0289 (14)
H17A	1.0442	0.7010	0.5825	0.035*
H17B	1.0810	0.8542	0.5486	0.035*
C18	1.1396 (3)	0.6591 (9)	0.6132 (4)	0.0301 (15)
H18A	1.1369	0.5333	0.6172	0.036*
H18B	1.1738	0.6866	0.5831	0.036*
C19	1.1551 (3)	0.7339 (11)	0.7131 (5)	0.0417 (18)
H19A	1.1947	0.6861	0.7499	0.063*
H19B	1.1217	0.7051	0.7436	0.063*
H19C	1.1588	0.8582	0.7096	0.063*
H3	0.622 (3)	0.919 (6)	−0.343 (5)	0.05 (2)*
H31	0.695 (5)	1.105 (16)	−0.006 (6)	0.16 (6)*
H32	0.714 (8)	1.266 (8)	0.059 (11)	0.22 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0141 (3)	0.0100 (3)	0.0124 (3)	−0.0002 (2)	0.0038 (2)	−0.0010 (2)
Cu2	0.0238 (5)	0.0127 (4)	0.0126 (4)	−0.0055 (4)	0.0041 (4)	0.0013 (3)
Cl1	0.0247 (7)	0.0129 (6)	0.0199 (6)	−0.0012 (5)	0.0051 (5)	−0.0045 (5)
Cl2	0.0362 (8)	0.0131 (6)	0.0223 (7)	0.0035 (6)	0.0000 (6)	−0.0011 (5)
O1	0.021 (2)	0.0137 (18)	0.0123 (18)	−0.0014 (15)	0.0064 (15)	−0.0017 (14)
O2	0.021 (2)	0.023 (2)	0.0146 (19)	−0.0062 (16)	0.0069 (16)	−0.0001 (15)
O3	0.051 (4)	0.075 (5)	0.042 (3)	−0.008 (3)	0.008 (3)	−0.007 (3)
N1	0.016 (2)	0.012 (2)	0.014 (2)	0.0021 (17)	0.0015 (17)	−0.0001 (17)
N2	0.013 (2)	0.017 (2)	0.015 (2)	−0.0003 (17)	0.0032 (17)	0.0002 (18)
N3	0.020 (2)	0.017 (2)	0.013 (2)	0.0017 (19)	0.0038 (18)	−0.0005 (18)
C1	0.021 (3)	0.006 (2)	0.017 (3)	0.001 (2)	0.003 (2)	0.0011 (19)
C2	0.020 (3)	0.011 (2)	0.020 (3)	0.005 (2)	0.003 (2)	0.005 (2)
C3	0.017 (3)	0.022 (3)	0.021 (3)	−0.001 (2)	0.009 (2)	0.001 (2)
C4	0.021 (3)	0.018 (3)	0.027 (3)	−0.005 (2)	0.010 (2)	0.001 (2)
C5	0.027 (3)	0.014 (3)	0.016 (3)	0.001 (2)	0.010 (2)	0.001 (2)
C6	0.023 (3)	0.016 (3)	0.009 (2)	0.002 (2)	0.000 (2)	−0.001 (2)
C7	0.018 (3)	0.015 (3)	0.019 (3)	−0.002 (2)	0.007 (2)	−0.008 (2)
C8	0.018 (3)	0.018 (3)	0.014 (3)	0.001 (2)	0.005 (2)	−0.001 (2)
C9	0.015 (3)	0.025 (3)	0.016 (3)	0.000 (2)	0.000 (2)	0.001 (2)
C10	0.021 (3)	0.034 (3)	0.023 (3)	0.007 (3)	−0.001 (2)	−0.008 (3)
C11	0.018 (3)	0.028 (3)	0.017 (3)	0.000 (2)	0.001 (2)	−0.002 (2)
C12	0.019 (3)	0.030 (3)	0.026 (3)	0.000 (3)	0.001 (2)	0.002 (3)
C13	0.022 (3)	0.034 (3)	0.022 (3)	−0.004 (3)	−0.002 (2)	0.006 (3)
C14	0.021 (3)	0.030 (3)	0.025 (3)	−0.002 (3)	0.001 (2)	0.004 (3)
C15	0.018 (3)	0.035 (4)	0.026 (3)	−0.002 (3)	−0.001 (2)	0.001 (3)
C16	0.019 (3)	0.035 (4)	0.026 (3)	−0.001 (3)	0.000 (2)	0.002 (3)
C17	0.025 (3)	0.034 (4)	0.024 (3)	−0.005 (3)	0.000 (2)	0.009 (3)
C18	0.021 (3)	0.034 (4)	0.030 (3)	−0.001 (3)	−0.002 (3)	0.007 (3)
C19	0.026 (3)	0.063 (5)	0.032 (4)	−0.004 (4)	0.000 (3)	−0.002 (4)

Geometric parameters (Å, º) top

Cu1—O1	1.962 (4)	C7—C8	1.495 (7)
Cu1—N3	1.986 (5)	C7—H7A	0.9900
Cu1—N1	2.041 (4)	C7—H7B	0.9900
Cu1—Cl1	2.2645 (14)	C9—C10	1.529 (7)
Cu1—N2	2.289 (4)	C9—H9A	0.9900
Cu2—O2	1.954 (4)	C9—H9B	0.9900
Cu2—O2ⁱ	1.954 (4)	C10—C11	1.526 (7)
Cu2—Cl2	2.2512 (14)	C10—H10A	0.9900
Cu2—Cl2ⁱ	2.2512 (15)	C10—H10B	0.9900
O1—C8	1.276 (6)	C11—C12	1.512 (7)
O2—C8	1.251 (6)	C11—H11A	0.9900
O3—H31	0.90 (2)	C11—H11B	0.9900
O3—H32	0.90 (2)	C12—C13	1.519 (8)
N1—C7	1.466 (7)	C12—H12A	0.9900
N1—C6	1.496 (6)	C12—H12B	0.9900
N1—C1	1.510 (6)	C13—C14	1.518 (8)
N2—C9	1.466 (6)	C13—H13A	0.9900
N2—C3	1.470 (7)	C13—H13B	0.9900
N2—C2	1.477 (6)	C14—C15	1.520 (8)
N3—C4	1.490 (7)	C14—H14A	0.9900
N3—C5	1.491 (7)	C14—H14B	0.9900
N3—H3	0.89 (2)	C15—C16	1.511 (8)
C1—C2	1.516 (7)	C15—H15A	0.9900
C1—H1A	0.9900	C15—H15B	0.9900
C1—H1B	0.9900	C16—C17	1.516 (8)
C2—H2A	0.9900	C16—H16A	0.9900
C2—H2B	0.9900	C16—H16B	0.9900
C3—C4	1.515 (8)	C17—C18	1.529 (8)
C3—H3A	0.9900	C17—H17A	0.9900
C3—H3B	0.9900	C17—H17B	0.9900
C4—H4A	0.9900	C18—C19	1.529 (9)
C4—H4B	0.9900	C18—H18A	0.9900
C5—C6	1.523 (7)	C18—H18B	0.9900
C5—H5A	0.9900	C19—H19A	0.9800
C5—H5B	0.9900	C19—H19B	0.9800
C6—H6A	0.9900	C19—H19C	0.9800
C6—H6B	0.9900

O1—Cu1—N3	164.51 (17)	N1—C7—H7A	109.3
O1—Cu1—N1	83.65 (16)	C8—C7—H7A	109.3
N3—Cu1—N1	85.07 (18)	N1—C7—H7B	109.3
O1—Cu1—Cl1	95.16 (11)	C8—C7—H7B	109.3
N3—Cu1—Cl1	94.70 (14)	H7A—C7—H7B	108.0
N1—Cu1—Cl1	172.72 (13)	O2—C8—O1	122.3 (5)
O1—Cu1—N2	107.10 (15)	O2—C8—C7	118.8 (5)
N3—Cu1—N2	82.35 (17)	O1—C8—C7	118.9 (5)
N1—Cu1—N2	84.80 (16)	N2—C9—C10	117.1 (5)
Cl1—Cu1—N2	102.39 (12)	N2—C9—H9A	108.0
O2—Cu2—O2ⁱ	180	C10—C9—H9A	108.0
O2—Cu2—Cl2	91.00 (12)	N2—C9—H9B	108.0
O2ⁱ—Cu2—Cl2	89.00 (12)	C10—C9—H9B	108.0
O2—Cu2—Cl2ⁱ	89.00 (12)	H9A—C9—H9B	107.3
O2ⁱ—Cu2—Cl2ⁱ	91.00 (12)	C11—C10—C9	110.5 (5)
Cl2—Cu2—Cl2ⁱ	180	C11—C10—H10A	109.5
C8—O1—Cu1	114.3 (3)	C9—C10—H10A	109.5
C8—O2—Cu2	114.2 (3)	C11—C10—H10B	109.5
H31—O3—H32	120 (10)	C9—C10—H10B	109.5
C7—N1—C6	112.5 (4)	H10A—C10—H10B	108.1
C7—N1—C1	111.7 (4)	C12—C11—C10	115.3 (5)
C6—N1—C1	112.2 (4)	C12—C11—H11A	108.5
C7—N1—Cu1	107.6 (3)	C10—C11—H11A	108.5
C6—N1—Cu1	103.4 (3)	C12—C11—H11B	108.5
C1—N1—Cu1	109.0 (3)	C10—C11—H11B	108.5
C9—N2—C3	112.7 (4)	H11A—C11—H11B	107.5
C9—N2—C2	113.1 (4)	C11—C12—C13	113.4 (5)
C3—N2—C2	114.7 (4)	C11—C12—H12A	108.9
C9—N2—Cu1	112.4 (3)	C13—C12—H12A	108.9
C3—N2—Cu1	105.0 (3)	C11—C12—H12B	108.9
C2—N2—Cu1	97.6 (3)	C13—C12—H12B	108.9
C4—N3—C5	113.8 (4)	H12A—C12—H12B	107.7
C4—N3—Cu1	106.8 (3)	C14—C13—C12	114.9 (5)
C5—N3—Cu1	111.4 (3)	C14—C13—H13A	108.5
C4—N3—H3	113 (5)	C12—C13—H13A	108.5
C5—N3—H3	101 (5)	C14—C13—H13B	108.5
Cu1—N3—H3	111 (5)	C12—C13—H13B	108.5
N1—C1—C2	112.9 (4)	H13A—C13—H13B	107.5
N1—C1—H1A	109.0	C13—C14—C15	113.4 (5)
C2—C1—H1A	109.0	C13—C14—H14A	108.9
N1—C1—H1B	109.0	C15—C14—H14A	108.9
C2—C1—H1B	109.0	C13—C14—H14B	108.9
H1A—C1—H1B	107.8	C15—C14—H14B	108.9
N2—C2—C1	112.0 (4)	H14A—C14—H14B	107.7
N2—C2—H2A	109.2	C16—C15—C14	114.3 (5)
C1—C2—H2A	109.2	C16—C15—H15A	108.7
N2—C2—H2B	109.2	C14—C15—H15A	108.7
C1—C2—H2B	109.2	C16—C15—H15B	108.7
H2A—C2—H2B	107.9	C14—C15—H15B	108.7
N2—C3—C4	110.5 (4)	H15A—C15—H15B	107.6
N2—C3—H3A	109.6	C15—C16—C17	114.0 (5)
C4—C3—H3A	109.6	C15—C16—H16A	108.8
N2—C3—H3B	109.6	C17—C16—H16A	108.8
C4—C3—H3B	109.6	C15—C16—H16B	108.8
H3A—C3—H3B	108.1	C17—C16—H16B	108.8
N3—C4—C3	110.6 (4)	H16A—C16—H16B	107.6
N3—C4—H4A	109.5	C16—C17—C18	114.2 (6)
C3—C4—H4A	109.5	C16—C17—H17A	108.7
N3—C4—H4B	109.5	C18—C17—H17A	108.7
C3—C4—H4B	109.5	C16—C17—H17B	108.7
H4A—C4—H4B	108.1	C18—C17—H17B	108.7
N3—C5—C6	109.8 (4)	H17A—C17—H17B	107.6
N3—C5—H5A	109.7	C19—C18—C17	112.2 (6)
C6—C5—H5A	109.7	C19—C18—H18A	109.2
N3—C5—H5B	109.7	C17—C18—H18A	109.2
C6—C5—H5B	109.7	C19—C18—H18B	109.2
H5A—C5—H5B	108.2	C17—C18—H18B	109.2
N1—C6—C5	109.0 (4)	H18A—C18—H18B	107.9
N1—C6—H6A	109.9	C18—C19—H19A	109.5
C5—C6—H6A	109.9	C18—C19—H19B	109.5
N1—C6—H6B	109.9	H19A—C19—H19B	109.5
C5—C6—H6B	109.9	C18—C19—H19C	109.5
H6A—C6—H6B	108.3	H19A—C19—H19C	109.5
N1—C7—C8	111.4 (4)	H19B—C19—H19C	109.5

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Cl1	0.90 (2)	2.37 (3)	3.267 (7)	172 (12)
N3—H3···Cl2ⁱⁱ	0.89 (2)	2.31 (3)	3.161 (5)	160 (7)

Symmetry code: (ii) −x+1, y+1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu₃Cl₄(C₁₇H₃₈N₃O₂)₂]·2H₂O
M_r	1049.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	22.1182 (11), 7.8330 (4), 14.6177 (7)
β (°)	104.570 (2)
V (Å³)	2451.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Bruker X8 APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.746, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	25491, 5625, 4994
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.142, 1.32
No. of reflections	5625
No. of parameters	271
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + 12.2399P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.62, −1.02

Computer programs: APEX2 (Bruker, 2005), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H31···Cl1	0.90 (2)	2.37 (3)	3.267 (7)	172 (12)
N3—H3···Cl2ⁱ	0.89 (2)	2.31 (3)	3.161 (5)	160 (7)

Symmetry code: (i) −x+1, y+1/2, −z−1/2.

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