Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061041/hg2329sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061041/hg2329Isup2.hkl |
CCDC reference: 672750
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
For related literature, see: Colacio et al. (2005); Meyer et al. (2005); Sarkar et al. (2004).
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.
H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C–H distances in the range 0.96–0.97 Å, N–H distances of 0.90 Å, and with Uiso(H) set to 1.2Ueq(C,N) and 1.5Ueq(methyl C).
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).
[Cu2(N3)4(C6H16N2)2][Cu(N3)2(C6H16N2)] | F(000) = 1644 |
Mr = 791.42 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 7614 independent reflections |
Radiation source: fine-focus sealed tube | 6149 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −28→29 |
Tmin = 0.768, Tmax = 0.836 | k = −16→16 |
28917 measured reflections | l = −14→14 |
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(Fo2) + (0.0428P)2 + 0.7266P] where P = (Fo2 + 2Fc2)/3 |
7614 reflections | (Δ/σ)max < 0.001 |
412 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Cu2(N3)4(C6H16N2)2][Cu(N3)2(C6H16N2)] | V = 3490.8 (5) Å3 |
Mr = 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)° |
Bruker SMART CCD area-detector diffractometer | 7614 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6149 reflections with I > 2σ(I) |
Tmin = 0.768, Tmax = 0.836 | Rint = 0.031 |
28917 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.44 e Å−3 |
7614 reflections | Δρmin = −0.31 e Å−3 |
412 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 | ||
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* |
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) |
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. |
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···N8iv | 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···N19v | 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)] |
Mr | 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) |
Tmin, Tmax | 0.768, 0.836 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28917, 7614, 6149 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.44, −0.31 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).
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. |
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···N19iv | 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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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).