Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036677/hy2071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036677/hy2071Isup2.hkl |
CCDC reference: 657640
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.028
- wR factor = 0.079
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang. PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 5.85 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu1 (2) 2.26
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The bond distances are similar to those reported in the literature (Hagrman et al., 1998).
Typically, CuSO4.5H2O (0.125 g, 0.5 mmol) was dispersed into DMF (10 ml) with stirring, then 2-aminopyridine (0.285 g, 0.3 mmol) was added to the above reaction mixture with stirring. The mixture with pH value of 5 was transferred into a 18 ml Teflon-lined stainless steel autoclave and heated at 353 K for 3 d. After cooling to room temperature, green block-shaped crystals of the title compound were obtained; they were filtered and washed thoroughly with deionized water and dried at room temperature.
All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C,N), and Uiso(H) = 1.5Ueq(C) for CH3 groups.
The title compound was obtained as the product of an attempted synthesis of an open-framework compound of copper(II) using 2-aminopyridine as structure-directing agent.
As shown in Fig. 1, the coordination polyhedron around the CuII atom is a distorted octahedron, comprising two O atoms from a bidentate sulfate anion, two N atoms from two 2-aminopyridine molecules and two O atoms from two N,N'-dimethylformamide (DMF) molecules. The bond distances are similar to those in the literature (Hagrman et al., 1998). There is a weak Cu1—O3 interaction of 2.589 (2)Å (Table 1). The molecules are connected by intermolecular hydrogen-bonding interactions (Table 2), resulting in a one-dimentional supramolecular structure (Fig. 2).
The bond distances are similar to those reported in the literature (Hagrman et al., 1998).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
[Cu(SO4)(C5H6N2)2(C3H7NO)2] | F(000) = 1028 |
Mr = 494.03 | Dx = 1.491 Mg m−3 |
Monoclinic, C2/c | Melting point: not measured K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.528 (5) Å | Cell parameters from 2666 reflections |
b = 18.156 (5) Å | θ = 2.1–28.3° |
c = 10.828 (5) Å | µ = 1.13 mm−1 |
β = 103.801 (5)° | T = 293 K |
V = 2200.9 (15) Å3 | Block, blue |
Z = 4 | 0.19 × 0.15 × 0.12 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2666 independent reflections |
Radiation source: fine-focus sealed tube | 2222 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→10 |
Tmin = 0.814, Tmax = 0.877 | k = −23→24 |
6718 measured reflections | l = −14→13 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.588P] where P = (Fo2 + 2Fc2)/3 |
2666 reflections | (Δ/σ)max < 0.001 |
139 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
[Cu(SO4)(C5H6N2)2(C3H7NO)2] | V = 2200.9 (15) Å3 |
Mr = 494.03 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.528 (5) Å | µ = 1.13 mm−1 |
b = 18.156 (5) Å | T = 293 K |
c = 10.828 (5) Å | 0.19 × 0.15 × 0.12 mm |
β = 103.801 (5)° |
Bruker SMART APEX CCD area-detector diffractometer | 2666 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2222 reflections with I > 2σ(I) |
Tmin = 0.814, Tmax = 0.877 | Rint = 0.023 |
6718 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.24 e Å−3 |
2666 reflections | Δρmin = −0.28 e Å−3 |
139 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.23305 (15) | 0.10448 (9) | 0.86610 (17) | 0.0350 (4) | |
C2 | 0.32604 (18) | 0.05410 (12) | 0.8644 (2) | 0.0531 (5) | |
H2 | 0.3957 | 0.0550 | 0.9289 | 0.064* | |
C3 | 0.3138 (2) | 0.00471 (13) | 0.7693 (3) | 0.0659 (7) | |
H3 | 0.3755 | −0.0278 | 0.7670 | 0.079* | |
C4 | 0.2086 (2) | 0.00265 (12) | 0.6749 (2) | 0.0636 (6) | |
H4 | 0.1983 | −0.0316 | 0.6093 | 0.076* | |
C5 | 0.12116 (19) | 0.05163 (10) | 0.68049 (18) | 0.0461 (4) | |
H5 | 0.0505 | 0.0499 | 0.6175 | 0.055* | |
C6 | 0.1553 (2) | 0.15450 (15) | 0.3507 (2) | 0.0672 (6) | |
H6A | 0.1303 | 0.1484 | 0.2630 | 0.101* | |
H6B | 0.1240 | 0.1169 | 0.3912 | 0.101* | |
H6C | 0.2383 | 0.1530 | 0.3750 | 0.101* | |
C7 | 0.1560 (2) | 0.29009 (15) | 0.3324 (2) | 0.0623 (6) | |
H7A | 0.1346 | 0.2874 | 0.2441 | 0.093* | |
H7B | 0.2387 | 0.2933 | 0.3600 | 0.093* | |
H7C | 0.1213 | 0.3316 | 0.3592 | 0.093* | |
C8 | 0.04146 (17) | 0.22969 (12) | 0.46322 (18) | 0.0437 (4) | |
H8 | 0.0197 | 0.2768 | 0.4830 | 0.052* | |
N1 | 0.13161 (12) | 0.10318 (7) | 0.77361 (13) | 0.0326 (3) | |
N2 | 0.24550 (13) | 0.15442 (9) | 0.95966 (16) | 0.0451 (4) | |
H2A | 0.1890 | 0.1852 | 0.9602 | 0.054* | |
H2B | 0.3100 | 0.1556 | 1.0191 | 0.054* | |
N3 | 0.11426 (14) | 0.22427 (10) | 0.38583 (15) | 0.0461 (4) | |
O1 | 0.10372 (10) | 0.26717 (6) | 0.76849 (12) | 0.0368 (3) | |
O2 | 0.01014 (11) | 0.36464 (7) | 0.86254 (12) | 0.0442 (3) | |
O3 | 0.00034 (14) | 0.17725 (8) | 0.51108 (14) | 0.0532 (4) | |
S1 | 0.0000 | 0.31992 (3) | 0.7500 | 0.02985 (13) | |
Cu1 | 0.0000 | 0.177216 (14) | 0.7500 | 0.03053 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0330 (8) | 0.0314 (8) | 0.0415 (9) | 0.0056 (7) | 0.0110 (7) | 0.0099 (7) |
C2 | 0.0419 (10) | 0.0495 (12) | 0.0673 (14) | 0.0179 (9) | 0.0121 (10) | 0.0141 (10) |
C3 | 0.0659 (15) | 0.0486 (12) | 0.0899 (18) | 0.0290 (11) | 0.0316 (13) | 0.0091 (12) |
C4 | 0.0897 (17) | 0.0407 (11) | 0.0663 (15) | 0.0180 (12) | 0.0302 (14) | −0.0085 (10) |
C5 | 0.0590 (11) | 0.0357 (9) | 0.0436 (10) | 0.0062 (8) | 0.0124 (9) | −0.0049 (8) |
C6 | 0.0670 (15) | 0.0732 (16) | 0.0676 (16) | 0.0154 (13) | 0.0286 (13) | −0.0051 (12) |
C7 | 0.0502 (12) | 0.0835 (17) | 0.0540 (13) | −0.0139 (12) | 0.0139 (10) | 0.0161 (12) |
C8 | 0.0419 (10) | 0.0525 (11) | 0.0377 (10) | 0.0039 (9) | 0.0117 (8) | 0.0025 (8) |
N1 | 0.0354 (7) | 0.0274 (7) | 0.0354 (7) | 0.0047 (5) | 0.0090 (6) | 0.0014 (5) |
N2 | 0.0373 (8) | 0.0498 (9) | 0.0421 (8) | 0.0074 (7) | −0.0023 (7) | −0.0039 (7) |
N3 | 0.0438 (9) | 0.0569 (10) | 0.0407 (9) | 0.0010 (8) | 0.0165 (7) | 0.0055 (7) |
O1 | 0.0250 (5) | 0.0303 (6) | 0.0537 (8) | 0.0004 (4) | 0.0064 (5) | −0.0001 (5) |
O2 | 0.0506 (7) | 0.0354 (7) | 0.0422 (7) | 0.0043 (6) | 0.0022 (6) | −0.0077 (5) |
O3 | 0.0549 (8) | 0.0605 (9) | 0.0497 (8) | −0.0010 (7) | 0.0234 (7) | 0.0091 (6) |
S1 | 0.0272 (3) | 0.0246 (3) | 0.0349 (3) | 0.000 | 0.0019 (2) | 0.000 |
Cu1 | 0.02611 (15) | 0.02407 (15) | 0.03997 (18) | 0.000 | 0.00507 (12) | 0.000 |
C1—N2 | 1.342 (2) | C7—H7B | 0.9300 |
C1—N1 | 1.346 (2) | C7—H7C | 0.9300 |
C1—C2 | 1.413 (2) | C8—O3 | 1.232 (2) |
C2—C3 | 1.347 (3) | C8—N3 | 1.324 (2) |
C2—H2 | 0.9300 | C8—H8 | 0.9300 |
C3—C4 | 1.388 (4) | N1—Cu1 | 1.9972 (14) |
C3—H3 | 0.9300 | N2—H2A | 0.8600 |
C4—C5 | 1.356 (3) | N2—H2B | 0.8600 |
C4—H4 | 0.9300 | O1—S1 | 1.5076 (13) |
C5—N1 | 1.360 (2) | O1—Cu1 | 2.0056 (13) |
C5—H5 | 0.9300 | O2—S1 | 1.4457 (13) |
C6—N3 | 1.435 (3) | O3—Cu1 | 2.589 (2) |
C6—H6A | 0.9300 | S1—O2i | 1.4457 (13) |
C6—H6B | 0.9300 | S1—O1i | 1.5076 (13) |
C6—H6C | 0.9300 | Cu1—N1i | 1.9972 (14) |
C7—N3 | 1.458 (3) | Cu1—O1i | 2.0056 (13) |
C7—H7A | 0.9300 | Cu1—O3i | 2.589 (2) |
N2—C1—N1 | 119.40 (15) | O3i—Cu1—N1 | 93.10 (6) |
N2—C1—C2 | 120.18 (17) | O3i—Cu1—N1i | 86.89 (6) |
N1—C1—C2 | 120.42 (17) | O3—Cu1—O1 | 87.47 (6) |
C3—C2—C1 | 120.0 (2) | O3i—Cu1—O1 | 92.47 (5) |
C3—C2—H2 | 120.0 | O3—Cu1—O1i | 92.47 (5) |
C1—C2—H2 | 120.0 | O3—Cu1—O3i | 179.99 (6) |
C2—C3—C4 | 119.6 (2) | O3i—Cu1—O1i | 87.47 (6) |
C2—C3—H3 | 120.2 | N3—C8—H8 | 117.5 |
C4—C3—H3 | 120.2 | C1—N1—C5 | 118.11 (15) |
C5—C4—C3 | 118.5 (2) | C1—N1—Cu1 | 125.59 (11) |
C5—C4—H4 | 120.7 | C5—N1—Cu1 | 115.99 (12) |
C3—C4—H4 | 120.7 | C1—N2—H2A | 120.0 |
N1—C5—C4 | 123.3 (2) | C1—N2—H2B | 120.0 |
N1—C5—H5 | 118.4 | H2A—N2—H2B | 120.0 |
C4—C5—H5 | 118.4 | C8—N3—C6 | 122.20 (19) |
N3—C6—H6A | 109.5 | C8—N3—C7 | 120.6 (2) |
N3—C6—H6B | 109.5 | C6—N3—C7 | 117.20 (19) |
H6A—C6—H6B | 109.5 | S1—O1—Cu1 | 93.96 (6) |
N3—C6—H6C | 109.5 | O2—S1—O2i | 111.66 (11) |
H6A—C6—H6C | 109.5 | O2—S1—O1 | 110.05 (7) |
H6B—C6—H6C | 109.5 | O2i—S1—O1 | 111.77 (7) |
N3—C7—H7A | 109.5 | O2—S1—O1i | 111.77 (7) |
N3—C7—H7B | 109.5 | O2i—S1—O1i | 110.05 (7) |
H7A—C7—H7B | 109.5 | O1—S1—O1i | 101.11 (10) |
N3—C7—H7C | 109.5 | N1i—Cu1—N1 | 95.40 (8) |
H7A—C7—H7C | 109.5 | N1i—Cu1—O1 | 167.79 (5) |
H7B—C7—H7C | 109.5 | N1—Cu1—O1 | 96.81 (6) |
O3—C8—N3 | 125.1 (2) | N1i—Cu1—O1i | 96.81 (6) |
O3—C8—H8 | 117.5 | N1—Cu1—O1i | 167.79 (5) |
O3—Cu1—N1 | 86.89 (6) | O1—Cu1—O1i | 70.97 (7) |
O3—Cu1—N1i | 93.10 (6) | ||
N2—C1—C2—C3 | −179.1 (2) | C5—N1—Cu1—O1i | −126.5 (2) |
N1—C1—C2—C3 | 0.5 (3) | C1—N1—Cu1—S1 | 47.13 (15) |
C1—C2—C3—C4 | −1.4 (4) | C5—N1—Cu1—S1 | −126.28 (12) |
C2—C3—C4—C5 | 0.9 (4) | S1—O1—Cu1—N1i | 0.2 (3) |
C3—C4—C5—N1 | 0.5 (3) | S1—O1—Cu1—N1 | −179.95 (6) |
N2—C1—N1—C5 | −179.56 (16) | S1—O1—Cu1—O1i | 0.0 |
C2—C1—N1—C5 | 0.9 (2) | O2—S1—Cu1—N1i | 91.32 (8) |
N2—C1—N1—Cu1 | 7.2 (2) | O2i—S1—Cu1—N1i | −88.68 (8) |
C2—C1—N1—Cu1 | −172.40 (13) | O1—S1—Cu1—N1i | −179.94 (8) |
C4—C5—N1—C1 | −1.4 (3) | O1i—S1—Cu1—N1i | 0.06 (8) |
C4—C5—N1—Cu1 | 172.55 (17) | O2—S1—Cu1—N1 | −88.68 (8) |
O3—C8—N3—C6 | −1.1 (3) | O2i—S1—Cu1—N1 | 91.32 (8) |
O3—C8—N3—C7 | 178.8 (2) | O1—S1—Cu1—N1 | 0.06 (8) |
Cu1—O1—S1—O2 | 118.29 (7) | O1i—S1—Cu1—N1 | −179.94 (8) |
Cu1—O1—S1—O2i | −117.04 (7) | O2—S1—Cu1—O1 | −88.75 (9) |
Cu1—O1—S1—O1i | 0.0 | O2i—S1—Cu1—O1 | 91.25 (9) |
C1—N1—Cu1—N1i | −132.87 (15) | O1i—S1—Cu1—O1 | 180.0 |
C5—N1—Cu1—N1i | 53.72 (12) | O2—S1—Cu1—O1i | 91.25 (9) |
C1—N1—Cu1—O1 | 47.16 (14) | O2i—S1—Cu1—O1i | −88.75 (9) |
C5—N1—Cu1—O1 | −126.24 (13) | O1—S1—Cu1—O1i | 180.0 |
C1—N1—Cu1—O1i | 47.0 (3) |
Symmetry code: (i) −x, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.55 | 3.087 (2) | 121 |
N2—H2A···O3i | 0.86 | 2.28 | 2.955 (2) | 135 |
N2—H2B···O2ii | 0.86 | 2.19 | 3.029 (2) | 164 |
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(SO4)(C5H6N2)2(C3H7NO)2] |
Mr | 494.03 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.528 (5), 18.156 (5), 10.828 (5) |
β (°) | 103.801 (5) |
V (Å3) | 2200.9 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.13 |
Crystal size (mm) | 0.19 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.814, 0.877 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6718, 2666, 2222 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.079, 1.05 |
No. of reflections | 2666 |
No. of parameters | 139 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.28 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.
N1—Cu1 | 1.9972 (14) | O3—Cu1 | 2.589 (2) |
O1—Cu1 | 2.0056 (13) | ||
O3—Cu1—N1 | 86.89 (6) | N1i—Cu1—N1 | 95.40 (8) |
O3—Cu1—N1i | 93.10 (6) | N1i—Cu1—O1 | 167.79 (5) |
O3—Cu1—O1 | 87.47 (6) | N1—Cu1—O1 | 96.81 (6) |
O3—Cu1—O1i | 92.47 (5) | O1—Cu1—O1i | 70.97 (7) |
O3—Cu1—O3i | 179.99 (6) |
Symmetry code: (i) −x, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.55 | 3.087 (2) | 121 |
N2—H2A···O3i | 0.86 | 2.28 | 2.955 (2) | 135 |
N2—H2B···O2ii | 0.86 | 2.19 | 3.029 (2) | 164 |
Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+2. |
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The title compound was obtained as the product of an attempted synthesis of an open-framework compound of copper(II) using 2-aminopyridine as structure-directing agent.
As shown in Fig. 1, the coordination polyhedron around the CuII atom is a distorted octahedron, comprising two O atoms from a bidentate sulfate anion, two N atoms from two 2-aminopyridine molecules and two O atoms from two N,N'-dimethylformamide (DMF) molecules. The bond distances are similar to those in the literature (Hagrman et al., 1998). There is a weak Cu1—O3 interaction of 2.589 (2)Å (Table 1). The molecules are connected by intermolecular hydrogen-bonding interactions (Table 2), resulting in a one-dimentional supramolecular structure (Fig. 2).