catena-Poly[{di-μ-azido-bis­[azido­(N,N-diethyl­ethane-1,2-diamine)copper(II)]} [[azido­(N,N-diethyl­ethane-1,2-diamine)copper(II)]-μ-azido]]

Yuan, C.-L.

doi:10.1107/S1600536807061041

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catena-Poly[{di-μ-azido-bis[azido(N,N-diethylethane-1,2-diamine)copper(II)]} [[azido(N,N-diethylethane-1,2-diamine)copper(II)]-μ-azido]]

C.-L. Yuan

The title complex, {[Cu₂(N₃)₄(C₆H₁₆N₂)₂][Cu(N₃)₂(C₆H₁₆N₂)]}_n, consists of an end-on azide-bridged dinuclear copper(II) complex and an end-to-end azide-bridged polynuclear copper(II) complex. Each Cu atom is five-coordinated by two N atoms of N,N-diethylethane-1,2-diamine and by three N atoms from three azide ligands, forming a slightly distorted square-pyramidal coordination environment.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061041/hg2329sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061041/hg2329Isup2.hkl Contains datablock I

CCDC reference: 672750

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.034
wR factor = 0.084
Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N20    -   N21     ..      11.29 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         N5
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        N14
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        N15

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.96 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N21    -   N22     ..       5.82 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   N9      ..       9.67 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N18
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24A   ..  N18     ..       2.67 Ang.

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  10 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
  12 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

Comment top

The azide anion is a versatile ligand that is able to link metal ions with different coordination modes, generating interesting polynuclear complexes (Colacio et al., 2005; Meyer et al., 2005; Sarkar et al., 2004). In this paper, a new azido-bridged copper(II) complex is reported.

The title complex consists of an end-on azido-bridged dinuclear copper(II) molecule (unit 1, Fig. 1) and an end-to-end azido-bridged polynuclear copper(II) molecule (unit 2, Fig. 2). Each Cu atom in unit 1 is in a square pyramidal coordination environment and is five-coordinated by two N atoms of N,N-diethylethane-1,2-diamine, one N atom of a terminal azido ligand, and one N atom of an end-on azido bridge, defining the basal plane, and by one N atom of another end-on azido bridge occupying the apical position. Each Cu atom in unit 2 is in a square pyramidal coordination environment and is five-coordinated by two N atoms of N,N-diethylethane-1,2-diamine, one N atom of a terminal azido ligand, and one N atom of an end-to-end azido bridge, defining the basal plane, and by one N atom of another end-to-end azido bridge occupying the apical position. The significant distortion of the square pyramids is revealed by the apical bond lengths (Cu1—N9 = 2.562 (2) Å, Cu2—N5 = 2.654 (2) Å, Cu3—N20 = 2.446 (2) Å), as well as the bond angles between the apical and basal donor atoms (Table 1).

Related literature top

For related literature, see: Colacio et al. (2005); Meyer et al. (2005); Sarkar et al. (2004).

Experimental top

N,N-Diethylethane-1,2-diamine (0.1 mmol, 11.6 mg), NaN₃ (0.2 mmol, 13.0 mg), and Cu(CH₃COO)₂.H₂O (0.1 mmol, 20.0 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 20 min to give a blue solution. The solution was kept in air for about a week, blue block-shaped crystals were formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

	Fig. 1. The structure of the dinuclear copper(II) molecule at the 30% probability level. H atoms have been omitted for clarity. Atoms labeled with the suffix A are at the symmetry position 1 - x, -y, 1 - z.
	Fig. 2. The structure of the polynuclear copper(II) molecule at the 30% probability level. H atoms have been omitted for clarity. Atoms labeled with the suffix B and C are at the symmetry positions x, 1/2 - y, 1/2 + z and x, 1/2 - y, -1/2 + z, respectively.

catena-Poly[{di-µ-azido-bis[azido(N,N-diethylethane-1,2-diamine)copper(II)]} [[azido(N,N-diethylethane-1,2-diamine)copper(II)]-µ-azido]] top

Crystal data top

[Cu₂(N₃)₄(C₆H₁₆N₂)₂][Cu(N₃)₂(C₆H₁₆N₂)]	F(000) = 1644
M_r = 791.42	D_x = 1.506 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8536 reflections
a = 22.722 (2) Å	θ = 2.3–25.7°
b = 13.2010 (12) Å	µ = 1.86 mm⁻¹
c = 11.6488 (10) Å	T = 298 K
β = 92.478 (2)°	Block, blue
V = 3490.8 (5) Å³	0.15 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	7614 independent reflections
Radiation source: fine-focus sealed tube	6149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→29
T_min = 0.768, T_max = 0.836	k = −16→16
28917 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0428P)² + 0.7266P] where P = (F_o² + 2F_c²)/3
7614 reflections	(Δ/σ)_max < 0.001
412 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu₂(N₃)₄(C₆H₁₆N₂)₂][Cu(N₃)₂(C₆H₁₆N₂)]	V = 3490.8 (5) Å³
M_r = 791.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.722 (2) Å	µ = 1.86 mm⁻¹
b = 13.2010 (12) Å	T = 298 K
c = 11.6488 (10) Å	0.15 × 0.12 × 0.10 mm
β = 92.478 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7614 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6149 reflections with I > 2σ(I)
T_min = 0.768, T_max = 0.836	R_int = 0.031
28917 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.02	Δρ_max = 0.44 e Å⁻³
7614 reflections	Δρ_min = −0.31 e Å⁻³
412 parameters

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	0.126741 (11)	0.15809 (2)	0.22935 (2)	0.03596 (8)
Cu2	0.213868 (13)	0.00077 (2)	−0.15330 (3)	0.04405 (9)
Cu3	0.463891 (12)	0.02522 (2)	0.38321 (2)	0.03575 (8)
N1	0.04653 (8)	0.09273 (15)	0.26784 (16)	0.0420 (5)
N2	0.09839 (8)	0.14681 (16)	0.06679 (16)	0.0421 (5)
H2C	0.1142	0.0932	0.0344	0.051*
H2D	0.1062	0.2048	0.0313	0.051*
N3	0.21109 (8)	0.15964 (17)	0.19209 (18)	0.0470 (5)
N4	0.23046 (9)	0.14004 (16)	0.10224 (19)	0.0454 (5)
N5	0.25194 (11)	0.1210 (2)	0.0168 (2)	0.0762 (8)
N6	0.14633 (9)	0.19101 (18)	0.39114 (17)	0.0517 (5)
N7	0.18555 (10)	0.15046 (17)	0.44386 (17)	0.0480 (5)
N8	0.22317 (13)	0.1135 (3)	0.4975 (2)	0.0846 (9)
N9	0.09411 (10)	0.34205 (18)	0.1973 (2)	0.0583 (6)
N10	0.11200 (8)	0.39817 (15)	0.26618 (18)	0.0409 (5)
N11	0.12909 (9)	0.45634 (16)	0.33842 (18)	0.0459 (5)
N12	0.23902 (8)	0.12097 (14)	−0.23815 (16)	0.0395 (4)
H12D	0.2213	0.1257	−0.3074	0.047*
H12E	0.2327	0.1785	−0.2012	0.047*
N13	0.29158 (8)	−0.06397 (15)	−0.20589 (17)	0.0411 (4)
N14	0.19881 (12)	−0.1125 (2)	−0.0533 (3)	0.0941 (11)
N15	0.15157 (11)	−0.12740 (18)	−0.0216 (2)	0.0630 (7)
N16	0.10672 (14)	−0.1438 (3)	0.0117 (3)	0.1171 (14)
N17	0.47984 (10)	−0.11053 (16)	0.32045 (19)	0.0525 (5)
N18	0.51569 (9)	−0.12911 (15)	0.25446 (18)	0.0446 (5)
N19	0.55073 (13)	−0.1515 (2)	0.1903 (3)	0.0886 (10)
N20	0.44968 (8)	−0.04691 (15)	0.57341 (16)	0.0394 (4)
N21	0.43106 (9)	−0.12899 (19)	0.57895 (18)	0.0492 (5)
N22	0.41048 (13)	−0.2094 (2)	0.5856 (2)	0.0776 (8)
N23	0.38086 (8)	0.03056 (14)	0.30150 (17)	0.0396 (4)
N24	0.44157 (8)	0.15731 (14)	0.45227 (16)	0.0389 (4)
H24A	0.4567	0.1632	0.5238	0.047*
H24B	0.4547	0.2103	0.4124	0.047*
C1	0.03390 (10)	0.1352 (2)	0.0643 (2)	0.0472 (6)
H1A	0.0195	0.1116	−0.0106	0.057*
H1B	0.0153	0.1995	0.0801	0.057*
C2	0.02024 (11)	0.0589 (2)	0.1552 (2)	0.0493 (6)
H2A	−0.0221	0.0521	0.1601	0.059*
H2B	0.0362	−0.0066	0.1354	0.059*
C3	0.00902 (11)	0.1712 (2)	0.3218 (2)	0.0560 (7)
H3A	0.0064	0.2292	0.2707	0.067*
H3B	0.0292	0.1935	0.3925	0.067*
C4	−0.05267 (14)	0.1405 (3)	0.3494 (3)	0.0835 (11)
H4A	−0.0515	0.0775	0.3907	0.125*
H4B	−0.0760	0.1324	0.2793	0.125*
H4C	−0.0698	0.1919	0.3957	0.125*
C5	0.05591 (14)	0.0050 (2)	0.3475 (3)	0.0676 (8)
H5A	0.0636	0.0307	0.4247	0.081*
H5B	0.0198	−0.0343	0.3478	0.081*
C6	0.10497 (17)	−0.0633 (3)	0.3182 (3)	0.0897 (11)
H6A	0.1414	−0.0263	0.3225	0.135*
H6B	0.0981	−0.0888	0.2416	0.135*
H6C	0.1072	−0.1188	0.3714	0.135*
C7	0.31562 (11)	0.00834 (17)	−0.2892 (2)	0.0409 (5)
H7A	0.2977	−0.0038	−0.3650	0.049*
H7B	0.3578	−0.0013	−0.2930	0.049*
C8	0.30298 (10)	0.11470 (18)	−0.2523 (2)	0.0411 (5)
H8A	0.3242	0.1300	−0.1803	0.049*
H8B	0.3149	0.1626	−0.3100	0.049*
C9	0.27930 (13)	−0.16364 (19)	−0.2597 (3)	0.0646 (8)
H9A	0.2714	−0.2124	−0.2001	0.077*
H9B	0.3141	−0.1862	−0.2979	0.077*
C10	0.22794 (16)	−0.1616 (3)	−0.3455 (4)	0.0951 (13)
H10A	0.1927	−0.1444	−0.3071	0.143*
H10B	0.2233	−0.2272	−0.3804	0.143*
H10C	0.2349	−0.1120	−0.4036	0.143*
C11	0.33289 (11)	−0.0760 (2)	−0.1028 (2)	0.0538 (7)
H11A	0.3146	−0.1212	−0.0492	0.065*
H11B	0.3372	−0.0106	−0.0656	0.065*
C12	0.39392 (12)	−0.1163 (3)	−0.1242 (3)	0.0697 (9)
H12A	0.3906	−0.1780	−0.1677	0.105*
H12B	0.4145	−0.1295	−0.0520	0.105*
H12C	0.4153	−0.0671	−0.1664	0.105*
C13	0.37677 (11)	0.16183 (18)	0.4497 (2)	0.0450 (6)
H13A	0.3637	0.2300	0.4662	0.054*
H13B	0.3615	0.1163	0.5066	0.054*
C14	0.35535 (10)	0.13047 (18)	0.3304 (2)	0.0448 (6)
H14A	0.3127	0.1262	0.3268	0.054*
H14B	0.3670	0.1808	0.2751	0.054*
C15	0.38632 (13)	0.0202 (2)	0.1756 (2)	0.0585 (7)
H15A	0.3492	0.0390	0.1373	0.070*
H15B	0.3938	−0.0503	0.1578	0.070*
C16	0.43467 (15)	0.0842 (3)	0.1286 (2)	0.0776 (10)
H16A	0.4720	0.0630	0.1623	0.116*
H16B	0.4280	0.1540	0.1469	0.116*
H16C	0.4348	0.0762	0.0467	0.116*
C17	0.34449 (11)	−0.05372 (19)	0.3482 (2)	0.0518 (6)
H17A	0.3410	−0.0426	0.4300	0.062*
H17B	0.3656	−0.1168	0.3392	0.062*
C18	0.28313 (13)	−0.0659 (2)	0.2937 (3)	0.0734 (9)
H18A	0.2858	−0.0895	0.2161	0.110*
H18B	0.2631	−0.0019	0.2936	0.110*
H18C	0.2615	−0.1142	0.3369	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03348 (15)	0.04709 (17)	0.02709 (14)	−0.00311 (12)	−0.00114 (10)	−0.00492 (11)
Cu2	0.03608 (16)	0.04575 (17)	0.05113 (19)	0.00447 (12)	0.01128 (13)	0.01752 (14)
Cu3	0.03740 (16)	0.03712 (15)	0.03270 (15)	0.01020 (11)	0.00123 (11)	−0.00185 (11)
N1	0.0427 (11)	0.0484 (12)	0.0350 (10)	−0.0087 (9)	0.0044 (8)	−0.0034 (9)
N2	0.0395 (11)	0.0551 (12)	0.0316 (10)	−0.0058 (9)	−0.0002 (8)	−0.0039 (9)
N3	0.0366 (11)	0.0612 (14)	0.0431 (12)	0.0001 (9)	0.0018 (9)	−0.0087 (10)
N4	0.0348 (11)	0.0548 (13)	0.0459 (13)	0.0093 (9)	−0.0040 (9)	0.0002 (10)
N5	0.0594 (16)	0.119 (2)	0.0513 (15)	0.0249 (16)	0.0086 (12)	−0.0064 (15)
N6	0.0507 (13)	0.0723 (15)	0.0314 (11)	0.0111 (11)	−0.0075 (9)	−0.0107 (10)
N7	0.0514 (13)	0.0641 (14)	0.0282 (10)	0.0056 (11)	−0.0014 (9)	−0.0085 (9)
N8	0.086 (2)	0.116 (2)	0.0500 (15)	0.0403 (18)	−0.0208 (14)	−0.0046 (15)
N9	0.0524 (14)	0.0558 (14)	0.0659 (15)	−0.0081 (11)	−0.0072 (12)	−0.0100 (12)
N10	0.0314 (10)	0.0387 (11)	0.0528 (13)	0.0008 (8)	0.0044 (9)	0.0040 (10)
N11	0.0385 (11)	0.0464 (12)	0.0532 (13)	−0.0030 (9)	0.0073 (9)	−0.0085 (10)
N12	0.0408 (11)	0.0354 (10)	0.0427 (11)	0.0016 (8)	0.0080 (9)	0.0030 (8)
N13	0.0401 (11)	0.0372 (10)	0.0463 (12)	0.0032 (8)	0.0064 (9)	0.0057 (9)
N14	0.0556 (16)	0.101 (2)	0.128 (3)	0.0149 (15)	0.0306 (17)	0.080 (2)
N15	0.0566 (15)	0.0602 (15)	0.0734 (17)	0.0057 (12)	0.0169 (13)	0.0356 (13)
N16	0.066 (2)	0.146 (3)	0.141 (3)	0.004 (2)	0.035 (2)	0.085 (3)
N17	0.0585 (14)	0.0463 (12)	0.0534 (13)	0.0087 (10)	0.0094 (11)	−0.0127 (10)
N18	0.0475 (12)	0.0403 (11)	0.0456 (12)	0.0081 (9)	−0.0030 (10)	−0.0131 (9)
N19	0.0780 (19)	0.079 (2)	0.112 (2)	−0.0036 (15)	0.0389 (18)	−0.0457 (17)
N20	0.0355 (10)	0.0427 (12)	0.0402 (11)	0.0075 (9)	0.0029 (8)	0.0026 (9)
N21	0.0480 (13)	0.0602 (15)	0.0398 (12)	0.0101 (11)	0.0072 (9)	−0.0040 (11)
N22	0.091 (2)	0.0576 (16)	0.085 (2)	−0.0149 (15)	0.0117 (16)	−0.0052 (14)
N23	0.0401 (11)	0.0404 (11)	0.0379 (11)	0.0067 (8)	−0.0033 (8)	0.0010 (8)
N24	0.0454 (11)	0.0373 (10)	0.0340 (10)	0.0082 (8)	0.0005 (8)	0.0016 (8)
C1	0.0398 (13)	0.0652 (16)	0.0359 (13)	−0.0071 (12)	−0.0069 (10)	−0.0055 (12)
C2	0.0459 (14)	0.0552 (16)	0.0468 (14)	−0.0145 (12)	0.0025 (11)	−0.0129 (12)
C3	0.0474 (15)	0.0690 (18)	0.0526 (16)	−0.0075 (13)	0.0125 (12)	−0.0159 (14)
C4	0.061 (2)	0.093 (3)	0.099 (3)	−0.0067 (18)	0.0331 (19)	−0.019 (2)
C5	0.072 (2)	0.069 (2)	0.063 (2)	−0.0116 (16)	0.0071 (16)	0.0169 (15)
C6	0.100 (3)	0.069 (2)	0.099 (3)	0.009 (2)	−0.004 (2)	0.027 (2)
C7	0.0424 (13)	0.0462 (13)	0.0346 (13)	0.0005 (10)	0.0074 (10)	0.0012 (10)
C8	0.0419 (13)	0.0407 (13)	0.0413 (13)	−0.0080 (10)	0.0075 (10)	0.0002 (10)
C9	0.0601 (18)	0.0366 (14)	0.097 (2)	−0.0001 (13)	0.0090 (17)	−0.0085 (14)
C10	0.085 (3)	0.070 (2)	0.129 (3)	−0.0171 (19)	−0.015 (2)	−0.037 (2)
C11	0.0515 (15)	0.0625 (17)	0.0477 (15)	0.0146 (13)	0.0056 (12)	0.0122 (13)
C12	0.0558 (18)	0.086 (2)	0.067 (2)	0.0210 (16)	0.0010 (15)	0.0128 (17)
C13	0.0462 (14)	0.0385 (13)	0.0512 (15)	0.0104 (10)	0.0118 (11)	−0.0005 (11)
C14	0.0394 (13)	0.0401 (13)	0.0544 (15)	0.0080 (10)	−0.0037 (11)	0.0058 (11)
C15	0.0596 (17)	0.075 (2)	0.0400 (15)	0.0117 (15)	−0.0098 (13)	−0.0014 (13)
C16	0.086 (2)	0.107 (3)	0.0405 (16)	0.004 (2)	0.0072 (15)	0.0144 (17)
C17	0.0493 (15)	0.0390 (13)	0.0669 (18)	0.0053 (11)	0.0023 (13)	0.0013 (12)
C18	0.0550 (18)	0.0513 (17)	0.113 (3)	−0.0033 (14)	−0.0038 (18)	−0.0035 (17)

Geometric parameters (Å, º) top

Cu1—N6	1.9663 (19)	C1—H1B	0.9700
Cu1—N2	1.9792 (18)	C2—H2A	0.9700
Cu1—N3	1.983 (2)	C2—H2B	0.9700
Cu1—N1	2.0827 (19)	C3—C4	1.507 (4)
Cu1—N9	2.562 (2)	C3—H3A	0.9700
Cu2—N5	2.654 (2)	C3—H3B	0.9700
Cu2—N14	1.936 (2)	C4—H4A	0.9600
Cu2—N12	1.9673 (18)	C4—H4B	0.9600
Cu2—N11ⁱ	2.006 (2)	C4—H4C	0.9600
Cu2—N13	2.0779 (19)	C5—C6	1.485 (5)
Cu3—N17	1.975 (2)	C5—H5A	0.9700
Cu3—N24	1.9950 (18)	C5—H5B	0.9700
Cu3—N20ⁱⁱ	2.0269 (19)	C6—H6A	0.9600
Cu3—N23	2.0773 (19)	C6—H6B	0.9600
Cu3—N20	2.4458 (19)	C6—H6C	0.9600
N1—C2	1.486 (3)	C7—C8	1.500 (3)
N1—C5	1.494 (3)	C7—H7A	0.9700
N1—C3	1.497 (3)	C7—H7B	0.9700
N2—C1	1.472 (3)	C8—H8A	0.9700
N2—H2C	0.9000	C8—H8B	0.9700
N2—H2D	0.9000	C9—C10	1.503 (4)
N3—N4	1.181 (3)	C9—H9A	0.9700
N4—N5	1.155 (3)	C9—H9B	0.9700
N6—N7	1.188 (3)	C10—H10A	0.9600
N7—N8	1.146 (3)	C10—H10B	0.9600
N9—N10	1.153 (3)	C10—H10C	0.9600
N10—N11	1.192 (3)	C11—C12	1.516 (4)
N11—Cu2ⁱⁱⁱ	2.006 (2)	C11—H11A	0.9700
N12—C8	1.472 (3)	C11—H11B	0.9700
N12—H12D	0.9000	C12—H12A	0.9600
N12—H12E	0.9000	C12—H12B	0.9600
N13—C9	1.479 (3)	C12—H12C	0.9600
N13—C7	1.482 (3)	C13—C14	1.511 (3)
N13—C11	1.500 (3)	C13—H13A	0.9700
N14—N15	1.167 (3)	C13—H13B	0.9700
N15—N16	1.127 (3)	C14—H14A	0.9700
N17—N18	1.170 (3)	C14—H14B	0.9700
N18—N19	1.154 (3)	C15—C16	1.507 (4)
N20—N21	1.166 (3)	C15—H15A	0.9700
N20—Cu3ⁱⁱ	2.0269 (19)	C15—H15B	0.9700
N21—N22	1.164 (3)	C16—H16A	0.9600
N23—C15	1.483 (3)	C16—H16B	0.9600
N23—C14	1.485 (3)	C16—H16C	0.9600
N23—C17	1.502 (3)	C17—C18	1.516 (4)
N24—C13	1.473 (3)	C17—H17A	0.9700
N24—H24A	0.9000	C17—H17B	0.9700
N24—H24B	0.9000	C18—H18A	0.9600
C1—C2	1.503 (4)	C18—H18B	0.9600
C1—H1A	0.9700	C18—H18C	0.9600

N6—Cu1—N2	169.89 (9)	C3—C4—H4A	109.5
N6—Cu1—N3	91.52 (9)	C3—C4—H4B	109.5
N2—Cu1—N3	93.96 (8)	H4A—C4—H4B	109.5
N6—Cu1—N1	92.82 (9)	C3—C4—H4C	109.5
N2—Cu1—N1	85.59 (8)	H4A—C4—H4C	109.5
N3—Cu1—N1	156.09 (8)	H4B—C4—H4C	109.5
N14—Cu2—N12	171.30 (12)	C6—C5—N1	114.6 (3)
N14—Cu2—N11ⁱ	93.02 (10)	C6—C5—H5A	108.6
N12—Cu2—N11ⁱ	92.72 (8)	N1—C5—H5A	108.6
N14—Cu2—N13	91.96 (10)	C6—C5—H5B	108.6
N12—Cu2—N13	85.10 (7)	N1—C5—H5B	108.6
N11ⁱ—Cu2—N13	158.19 (9)	H5A—C5—H5B	107.6
N17—Cu3—N24	175.07 (9)	C5—C6—H6A	109.5
N17—Cu3—N20ⁱⁱ	91.67 (9)	C5—C6—H6B	109.5
N24—Cu3—N20ⁱⁱ	92.09 (8)	H6A—C6—H6B	109.5
N17—Cu3—N23	92.22 (8)	C5—C6—H6C	109.5
N24—Cu3—N23	85.03 (8)	H6A—C6—H6C	109.5
N20ⁱⁱ—Cu3—N23	163.83 (8)	H6B—C6—H6C	109.5
N17—Cu3—N20	90.89 (8)	N13—C7—C8	109.56 (18)
N24—Cu3—N20	85.94 (7)	N13—C7—H7A	109.8
N20ⁱⁱ—Cu3—N20	89.64 (7)	C8—C7—H7A	109.8
N23—Cu3—N20	105.99 (7)	N13—C7—H7B	109.8
C2—N1—C5	110.9 (2)	C8—C7—H7B	109.8
C2—N1—C3	111.3 (2)	H7A—C7—H7B	108.2
C5—N1—C3	110.1 (2)	N12—C8—C7	106.67 (18)
C2—N1—Cu1	104.86 (14)	N12—C8—H8A	110.4
C5—N1—Cu1	110.64 (17)	C7—C8—H8A	110.4
C3—N1—Cu1	108.84 (15)	N12—C8—H8B	110.4
C1—N2—Cu1	107.99 (14)	C7—C8—H8B	110.4
C1—N2—H2C	109.3	H8A—C8—H8B	108.6
Cu1—N2—H2C	110.3	N13—C9—C10	113.1 (2)
C1—N2—H2D	107.4	N13—C9—H9A	109.0
Cu1—N2—H2D	108.4	C10—C9—H9A	109.0
H2C—N2—H2D	113.3	N13—C9—H9B	109.0
N4—N3—Cu1	126.31 (17)	C10—C9—H9B	109.0
N5—N4—N3	176.9 (3)	H9A—C9—H9B	107.8
N7—N6—Cu1	121.99 (17)	C9—C10—H10A	109.5
N8—N7—N6	177.8 (3)	C9—C10—H10B	109.5
N9—N10—N11	178.3 (2)	H10A—C10—H10B	109.5
N10—N11—Cu2ⁱⁱⁱ	119.92 (16)	C9—C10—H10C	109.5
C8—N12—Cu2	108.69 (14)	H10A—C10—H10C	109.5
C8—N12—H12D	108.3	H10B—C10—H10C	109.5
Cu2—N12—H12D	112.5	N13—C11—C12	116.8 (2)
C8—N12—H12E	106.4	N13—C11—H11A	108.1
Cu2—N12—H12E	113.0	C12—C11—H11A	108.1
H12D—N12—H12E	107.7	N13—C11—H11B	108.1
C9—N13—C7	111.3 (2)	C12—C11—H11B	108.1
C9—N13—C11	110.2 (2)	H11A—C11—H11B	107.3
C7—N13—C11	110.90 (19)	C11—C12—H12A	109.5
C9—N13—Cu2	110.11 (16)	C11—C12—H12B	109.5
C7—N13—Cu2	105.66 (14)	H12A—C12—H12B	109.5
C11—N13—Cu2	108.55 (14)	C11—C12—H12C	109.5
N15—N14—Cu2	120.6 (2)	H12A—C12—H12C	109.5
N16—N15—N14	177.8 (3)	H12B—C12—H12C	109.5
N18—N17—Cu3	125.29 (19)	N24—C13—C14	106.84 (19)
N19—N18—N17	177.3 (3)	N24—C13—H13A	110.4
N21—N20—Cu3ⁱⁱ	117.87 (17)	C14—C13—H13A	110.4
N21—N20—Cu3	118.31 (16)	N24—C13—H13B	110.4
Cu3ⁱⁱ—N20—Cu3	90.36 (7)	C14—C13—H13B	110.4
N22—N21—N20	177.5 (3)	H13A—C13—H13B	108.6
C15—N23—C14	110.84 (19)	N23—C14—C13	109.77 (18)
C15—N23—C17	111.2 (2)	N23—C14—H14A	109.7
C14—N23—C17	110.46 (19)	C13—C14—H14A	109.7
C15—N23—Cu3	109.68 (16)	N23—C14—H14B	109.7
C14—N23—Cu3	106.38 (14)	C13—C14—H14B	109.7
C17—N23—Cu3	108.16 (14)	H14A—C14—H14B	108.2
C13—N24—Cu3	107.38 (14)	N23—C15—C16	113.7 (2)
C13—N24—H24A	111.2	N23—C15—H15A	108.8
Cu3—N24—H24A	111.0	C16—C15—H15A	108.8
C13—N24—H24B	108.2	N23—C15—H15B	108.8
Cu3—N24—H24B	112.1	C16—C15—H15B	108.8
H24A—N24—H24B	107.0	H15A—C15—H15B	107.7
N2—C1—C2	107.0 (2)	C15—C16—H16A	109.5
N2—C1—H1A	110.3	C15—C16—H16B	109.5
C2—C1—H1A	110.3	H16A—C16—H16B	109.5
N2—C1—H1B	110.3	C15—C16—H16C	109.5
C2—C1—H1B	110.3	H16A—C16—H16C	109.5
H1A—C1—H1B	108.6	H16B—C16—H16C	109.5
N1—C2—C1	109.48 (19)	N23—C17—C18	115.9 (2)
N1—C2—H2A	109.8	N23—C17—H17A	108.3
C1—C2—H2A	109.8	C18—C17—H17A	108.3
N1—C2—H2B	109.8	N23—C17—H17B	108.3
C1—C2—H2B	109.8	C18—C17—H17B	108.3
H2A—C2—H2B	108.2	H17A—C17—H17B	107.4
N1—C3—C4	117.1 (2)	C17—C18—H18A	109.5
N1—C3—H3A	108.0	C17—C18—H18B	109.5
C4—C3—H3A	108.0	H18A—C18—H18B	109.5
N1—C3—H3B	108.0	C17—C18—H18C	109.5
C4—C3—H3B	108.0	H18A—C18—H18C	109.5
H3A—C3—H3B	107.3	H18B—C18—H18C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···N11ⁱ	0.89	2.41	3.095 (3)	134
N2—H2D···N6ⁱ	0.89	2.35	3.186 (3)	156
N12—H12D···N8^iv	0.89	2.28	3.087 (3)	151
N12—H12E···N3ⁱ	0.89	2.51	3.067 (3)	121
N24—H24A···N17ⁱⁱ	0.89	2.37	3.189 (3)	153
N24—H24A···N18ⁱⁱ	0.89	2.67	3.531 (3)	163
N24—H24B···N19^v	0.90	2.18	3.031 (3)	157

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

Experimental details

Crystal data
Chemical formula	[Cu₂(N₃)₄(C₆H₁₆N₂)₂][Cu(N₃)₂(C₆H₁₆N₂)]
M_r	791.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	22.722 (2), 13.2010 (12), 11.6488 (10)
β (°)	92.478 (2)
V (Å³)	3490.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.768, 0.836
No. of measured, independent and observed [I > 2σ(I)] reflections	28917, 7614, 6149
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.084, 1.02
No. of reflections	7614
No. of parameters	412
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.31

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).

Selected geometric parameters (Å, º) top

Cu1—N6	1.9663 (19)	Cu2—N11ⁱ	2.006 (2)
Cu1—N2	1.9792 (18)	Cu2—N13	2.0779 (19)
Cu1—N3	1.983 (2)	Cu3—N17	1.975 (2)
Cu1—N1	2.0827 (19)	Cu3—N24	1.9950 (18)
Cu1—N9	2.562 (2)	Cu3—N20ⁱⁱ	2.0269 (19)
Cu2—N5	2.654 (2)	Cu3—N23	2.0773 (19)
Cu2—N14	1.936 (2)	Cu3—N20	2.4458 (19)
Cu2—N12	1.9673 (18)

N6—Cu1—N2	169.89 (9)	N11ⁱ—Cu2—N13	158.19 (9)
N6—Cu1—N3	91.52 (9)	N17—Cu3—N24	175.07 (9)
N2—Cu1—N3	93.96 (8)	N17—Cu3—N20ⁱⁱ	91.67 (9)
N6—Cu1—N1	92.82 (9)	N24—Cu3—N20ⁱⁱ	92.09 (8)
N2—Cu1—N1	85.59 (8)	N17—Cu3—N23	92.22 (8)
N3—Cu1—N1	156.09 (8)	N24—Cu3—N23	85.03 (8)
N14—Cu2—N12	171.30 (12)	N20ⁱⁱ—Cu3—N23	163.83 (8)
N14—Cu2—N11ⁱ	93.02 (10)	N17—Cu3—N20	90.89 (8)
N12—Cu2—N11ⁱ	92.72 (8)	N24—Cu3—N20	85.94 (7)
N14—Cu2—N13	91.96 (10)	N20ⁱⁱ—Cu3—N20	89.64 (7)
N12—Cu2—N13	85.10 (7)	N23—Cu3—N20	105.99 (7)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···N11ⁱ	0.89	2.41	3.095 (3)	134
N2—H2D···N6ⁱ	0.89	2.35	3.186 (3)	156
N12—H12D···N8ⁱⁱⁱ	0.89	2.28	3.087 (3)	151
N12—H12E···N3ⁱ	0.89	2.51	3.067 (3)	121
N24—H24A···N17ⁱⁱ	0.89	2.37	3.189 (3)	153
N24—H24A···N18ⁱⁱ	0.89	2.67	3.531 (3)	163
N24—H24B···N19^iv	0.90	2.18	3.031 (3)	157

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

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