Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022702/lh2383sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022702/lh2383Isup2.hkl |
CCDC reference: 650624
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.027
- wR factor = 0.077
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.606 0.784 Tmin(prime) and Tmax expected: 0.704 0.774 RR(prime) = 0.850 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 18
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
There are no crystal structure reports of metal 5-(2-pyrazinyl)-5H-tetrazolates. For the crystal structure of the hemihydrated organic compound, see: Li et al., 2007.
For related literature, see: Allen (2002).
Copper chloride dihydrate (34 mg, 0.2 mmol) and 2-(1H-tetrazol-5-yl)pyrazine (60 mg, 0.4 mmol) were dissolved in 10 ml of a DMF–water (1:1) mixture. The clear solution was filtered; blue crystals were isolated after a month in 30% yield.
Carbon-bound H atoms were placed at calculated positions [C—H = 0.93 Å; U(H) = 1.2Ueq(C)]. The O2w atom is disordered about a twofold axis, and it was allowed to refine off the symmetry element. The H atoms of the water molecules were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85±0.01 Å and H···H = 1.39±0.01 Å.
The Cambridge Structural Database (Version 5.28, November 2006; Allen, 2002) lists several examples of metal 5-(2-pyridyl)-5H-tetrazoles. A second nitrogen donor site in a pyrazine ring group could serve as a donor site, but this is not observed in the copper derivative, which crystallizes as a diaqua monohydrate. The second donor site in the pyrimidyl part of the anion is engaged in hydrogen bonding with the coordinated and lattice water molecules to form a three-dimensional network motif.
There are no crystal structure reports of metal 5-(2-pyrazinyl)-5H-tetrazolates. For the crystal structure of the hemihydrated organic compound, see: Li et al., 2007.
For related literature, see: Allen (2002).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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: publCIF (Westrip, 2007).
[Cu(C5H3N6)2(H2O)2]·H2O | F(000) = 836 |
Mr = 411.86 | Dx = 1.730 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2454 reflections |
a = 13.045 (2) Å | θ = 3.2–26.3° |
b = 7.341 (1) Å | µ = 1.43 mm−1 |
c = 16.869 (2) Å | T = 294 K |
β = 101.757 (2)° | Block, blue |
V = 1581.5 (4) Å3 | 0.24 × 0.22 × 0.18 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 1603 independent reflections |
Radiation source: fine-focus sealed tube | 1375 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→16 |
Tmin = 0.606, Tmax = 0.784 | k = −9→9 |
4287 measured reflections | l = −14→20 |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0428P)2 + 1.3231P] where P = (Fo2 + 2Fc2)/3 |
1603 reflections | (Δ/σ)max = 0.001 |
136 parameters | Δρmax = 0.31 e Å−3 |
18 restraints | Δρmin = −0.27 e Å−3 |
[Cu(C5H3N6)2(H2O)2]·H2O | V = 1581.5 (4) Å3 |
Mr = 411.86 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.045 (2) Å | µ = 1.43 mm−1 |
b = 7.341 (1) Å | T = 294 K |
c = 16.869 (2) Å | 0.24 × 0.22 × 0.18 mm |
β = 101.757 (2)° |
Bruker APEX area-detector diffractometer | 1603 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1375 reflections with I > 2σ(I) |
Tmin = 0.606, Tmax = 0.784 | Rint = 0.027 |
4287 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 18 restraints |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.31 e Å−3 |
1603 reflections | Δρmin = −0.27 e Å−3 |
136 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.02729 (14) | |
O1W | 0.60924 (12) | 0.6371 (2) | 0.41419 (10) | 0.0387 (4) | |
H11 | 0.6673 (11) | 0.582 (3) | 0.4237 (16) | 0.046* | |
H12 | 0.6171 (17) | 0.7461 (16) | 0.4309 (15) | 0.046* | |
O2W | 0.5303 (4) | 0.6846 (6) | 0.2457 (5) | 0.0821 (19) | 0.50 |
H21 | 0.556 (5) | 0.660 (7) | 0.2958 (15) | 0.099* | 0.50 |
H22 | 0.508 (7) | 0.583 (5) | 0.223 (3) | 0.099* | 0.50 |
N1 | 0.40820 (12) | 0.7190 (2) | 0.48450 (10) | 0.0267 (4) | |
N2 | 0.32571 (13) | 0.7878 (2) | 0.43186 (11) | 0.0322 (4) | |
N3 | 0.30323 (14) | 0.9464 (3) | 0.45989 (12) | 0.0337 (4) | |
N4 | 0.36960 (15) | 0.9853 (2) | 0.53077 (12) | 0.0318 (4) | |
N5 | 0.57264 (12) | 0.6487 (2) | 0.59883 (10) | 0.0281 (4) | |
N6 | 0.64382 (16) | 0.8787 (3) | 0.72971 (12) | 0.0460 (5) | |
C1 | 0.43250 (14) | 0.8413 (2) | 0.54351 (12) | 0.0251 (4) | |
C2 | 0.52281 (15) | 0.8057 (3) | 0.60846 (12) | 0.0261 (4) | |
C3 | 0.55893 (18) | 0.9186 (3) | 0.67355 (14) | 0.0364 (5) | |
H3 | 0.5230 | 1.0261 | 0.6784 | 0.044* | |
C4 | 0.6933 (2) | 0.7251 (3) | 0.71873 (15) | 0.0474 (6) | |
H4 | 0.7536 | 0.6941 | 0.7561 | 0.057* | |
C5 | 0.65859 (17) | 0.6091 (3) | 0.65368 (14) | 0.0384 (5) | |
H5 | 0.6956 | 0.5031 | 0.6484 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0274 (2) | 0.0203 (2) | 0.0296 (2) | 0.00697 (13) | −0.00475 (14) | −0.00489 (14) |
O1W | 0.0332 (8) | 0.0308 (8) | 0.0497 (10) | 0.0062 (6) | 0.0030 (7) | −0.0004 (7) |
O2W | 0.100 (5) | 0.073 (3) | 0.064 (3) | −0.024 (3) | −0.006 (4) | 0.005 (3) |
N1 | 0.0247 (8) | 0.0226 (8) | 0.0306 (9) | 0.0042 (6) | 0.0005 (7) | 0.0001 (7) |
N2 | 0.0278 (8) | 0.0293 (9) | 0.0368 (10) | 0.0066 (7) | 0.0003 (7) | 0.0029 (8) |
N3 | 0.0300 (9) | 0.0277 (9) | 0.0425 (10) | 0.0070 (7) | 0.0051 (8) | 0.0039 (8) |
N4 | 0.0310 (9) | 0.0233 (9) | 0.0416 (10) | 0.0048 (7) | 0.0089 (8) | 0.0007 (7) |
N5 | 0.0274 (8) | 0.0234 (8) | 0.0310 (9) | 0.0018 (7) | −0.0001 (7) | −0.0036 (7) |
N6 | 0.0512 (12) | 0.0410 (12) | 0.0397 (11) | −0.0005 (9) | −0.0054 (9) | −0.0108 (9) |
C1 | 0.0246 (9) | 0.0203 (9) | 0.0315 (10) | 0.0020 (7) | 0.0080 (8) | −0.0003 (8) |
C2 | 0.0267 (9) | 0.0222 (10) | 0.0298 (10) | −0.0013 (7) | 0.0064 (8) | −0.0014 (8) |
C3 | 0.0414 (12) | 0.0305 (12) | 0.0366 (12) | 0.0019 (10) | 0.0066 (10) | −0.0067 (10) |
C4 | 0.0448 (13) | 0.0423 (14) | 0.0449 (14) | 0.0044 (11) | −0.0149 (11) | −0.0082 (11) |
C5 | 0.0357 (12) | 0.0320 (12) | 0.0412 (13) | 0.0057 (9) | −0.0068 (10) | −0.0035 (10) |
Cu1—N1 | 1.990 (2) | N3—N4 | 1.356 (3) |
Cu1—N1i | 1.990 (2) | N4—C1 | 1.328 (2) |
Cu1—N5 | 2.056 (2) | N5—C5 | 1.332 (3) |
Cu1—N5i | 2.056 (2) | N5—C2 | 1.349 (2) |
Cu1—O1w | 2.445 (2) | N6—C4 | 1.331 (3) |
O1W—H11 | 0.84 (1) | N6—C3 | 1.335 (3) |
O1W—H12 | 0.85 (1) | C1—C2 | 1.460 (3) |
O2W—H21 | 0.86 (1) | C2—C3 | 1.380 (3) |
O2W—H22 | 0.86 (1) | C3—H3 | 0.9300 |
N1—C1 | 1.330 (2) | C4—C5 | 1.390 (3) |
N1—N2 | 1.346 (2) | C4—H4 | 0.9300 |
N2—N3 | 1.312 (3) | C5—H5 | 0.9300 |
N1i—Cu1—N1 | 180.000 (1) | C5—N5—C2 | 117.45 (18) |
N1i—Cu1—N5i | 80.97 (6) | C5—N5—Cu1 | 129.11 (14) |
N1—Cu1—N5i | 99.03 (6) | C2—N5—Cu1 | 113.42 (13) |
N1i—Cu1—N5 | 99.03 (6) | C4—N6—C3 | 116.3 (2) |
N1—Cu1—N5 | 80.97 (6) | N4—C1—N1 | 111.76 (17) |
N5i—Cu1—N5 | 180.0 | N4—C1—C2 | 129.91 (18) |
N1i—Cu1—O1W | 90.14 (6) | N1—C1—C2 | 118.27 (16) |
N1—Cu1—O1W | 89.86 (6) | N5—C2—C3 | 120.95 (18) |
N5i—Cu1—O1W | 88.07 (6) | N5—C2—C1 | 113.44 (17) |
N5—Cu1—O1W | 91.93 (6) | C3—C2—C1 | 125.58 (18) |
Cu1—O1W—H11 | 107.4 (18) | N6—C3—C2 | 122.1 (2) |
Cu1—O1W—H12 | 103.7 (17) | N6—C3—H3 | 118.9 |
H11—O1W—H12 | 110.1 (15) | C2—C3—H3 | 118.9 |
H21—O2W—H22 | 106.4 (17) | N6—C4—C5 | 122.6 (2) |
C1—N1—N2 | 106.08 (15) | N6—C4—H4 | 118.7 |
C1—N1—Cu1 | 113.68 (12) | C5—C4—H4 | 118.7 |
N2—N1—Cu1 | 140.23 (13) | N5—C5—C4 | 120.5 (2) |
N3—N2—N1 | 107.61 (16) | N5—C5—H5 | 119.8 |
N2—N3—N4 | 110.81 (16) | C4—C5—H5 | 119.8 |
C1—N4—N3 | 103.74 (16) | ||
N5i—Cu1—N1—C1 | 176.48 (13) | Cu1—N1—C1—N4 | 179.87 (13) |
N5—Cu1—N1—C1 | −3.52 (13) | N2—N1—C1—C2 | −177.69 (17) |
O1W—Cu1—N1—C1 | −95.49 (14) | Cu1—N1—C1—C2 | 2.4 (2) |
N5i—Cu1—N1—N2 | −3.3 (2) | C5—N5—C2—C3 | −1.1 (3) |
N5—Cu1—N1—N2 | 176.7 (2) | Cu1—N5—C2—C3 | 177.58 (16) |
O1W—Cu1—N1—N2 | 84.7 (2) | C5—N5—C2—C1 | 177.32 (18) |
C1—N1—N2—N3 | 0.1 (2) | Cu1—N5—C2—C1 | −4.0 (2) |
Cu1—N1—N2—N3 | 179.95 (16) | N4—C1—C2—N5 | −175.75 (19) |
N1—N2—N3—N4 | 0.0 (2) | N1—C1—C2—N5 | 1.1 (3) |
N2—N3—N4—C1 | −0.2 (2) | N4—C1—C2—C3 | 2.6 (3) |
N1i—Cu1—N5—C5 | 2.7 (2) | N1—C1—C2—C3 | 179.5 (2) |
N1—Cu1—N5—C5 | −177.3 (2) | C4—N6—C3—C2 | 1.3 (4) |
O1W—Cu1—N5—C5 | −87.79 (19) | N5—C2—C3—N6 | −0.2 (3) |
N1i—Cu1—N5—C2 | −175.81 (14) | C1—C2—C3—N6 | −178.4 (2) |
N1—Cu1—N5—C2 | 4.19 (14) | C3—N6—C4—C5 | −1.3 (4) |
O1W—Cu1—N5—C2 | 93.74 (14) | C2—N5—C5—C4 | 1.1 (3) |
N3—N4—C1—N1 | 0.3 (2) | Cu1—N5—C5—C4 | −177.28 (18) |
N3—N4—C1—C2 | 177.32 (19) | N6—C4—C5—N5 | 0.0 (4) |
N2—N1—C1—N4 | −0.3 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H11···N3ii | 0.84 (1) | 2.02 (1) | 2.857 (2) | 173 (3) |
O1w—H12···N4iii | 0.85 (1) | 2.07 (1) | 2.919 (2) | 178 (2) |
O2w—H21···O1w | 0.86 (1) | 1.98 (2) | 2.841 (9) | 172 (6) |
Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C5H3N6)2(H2O)2]·H2O |
Mr | 411.86 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 13.045 (2), 7.341 (1), 16.869 (2) |
β (°) | 101.757 (2) |
V (Å3) | 1581.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.43 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker APEX area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.606, 0.784 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4287, 1603, 1375 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.077, 1.02 |
No. of reflections | 1603 |
No. of parameters | 136 |
No. of restraints | 18 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.27 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H11···N3i | 0.84 (1) | 2.02 (1) | 2.857 (2) | 173 (3) |
O1w—H12···N4ii | 0.85 (1) | 2.07 (1) | 2.919 (2) | 178 (2) |
O2w—H21···O1w | 0.86 (1) | 1.98 (2) | 2.841 (9) | 172 (6) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+1, −y+2, −z+1. |
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The Cambridge Structural Database (Version 5.28, November 2006; Allen, 2002) lists several examples of metal 5-(2-pyridyl)-5H-tetrazoles. A second nitrogen donor site in a pyrazine ring group could serve as a donor site, but this is not observed in the copper derivative, which crystallizes as a diaqua monohydrate. The second donor site in the pyrimidyl part of the anion is engaged in hydrogen bonding with the coordinated and lattice water molecules to form a three-dimensional network motif.