metal-organic compounds
The title compound, [CuBr(C3H4N2)2(C10H8N2)]Br, consists of bromodiimidazole(2,2'-bipyridine)copper(II) cations and bromide anions that are linked by hydrogen bonds into a network structure. Two imidazoles, a 2,2'-bipyridine and a bromide anion are coordinated by the Cu atom, whose geometry is distorted towards octahedral because of the second bromide anion.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030284/ng6059sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030284/ng6059Isup2.hkl |
CCDC reference: 259078
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
(I) top
Crystal data top
[Cu(C10H8N2)(C3H4N2)2Br].Br | F(000) = 1012.0 |
Mr = 515.71 | Dx = 1.861 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3180 reflections |
a = 13.121 (5) Å | θ = 1.6–25.1° |
b = 8.731 (3) Å | µ = 5.54 mm−1 |
c = 16.205 (6) Å | T = 298 K |
β = 97.560 (6)° | Prism, blue |
V = 1840.2 (11) Å3 | 0.25 × 0.19 × 0.15 mm |
Z = 4 |
Data collection top
Bruker APEX area-detector diffractometer | 3180 independent reflections |
Radiation source: fine-focus sealed tube | 2536 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 25.1°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −15→10 |
Tmin = 0.50, Tmax = 0.82 | k = −10→10 |
8504 measured reflections | l = −18→19 |
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) = 0.108 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.065P)2] where P = (Fo2 + 2Fc2)/3 |
3180 reflections | (Δ/σ)max = 0.001 |
226 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.81906 (4) | 0.54969 (5) | −0.00362 (3) | 0.05326 (18) | |
Br2 | 0.70482 (3) | 0.02184 (6) | 0.21618 (3) | 0.04965 (18) | |
Cu1 | 0.77800 (3) | 0.29466 (6) | 0.09347 (3) | 0.03975 (18) | |
N1 | 0.6332 (2) | 0.2670 (4) | 0.0334 (2) | 0.0360 (8) | |
N3 | 0.9127 (2) | 0.3087 (4) | 0.1670 (2) | 0.0380 (8) | |
N5 | 0.8347 (2) | 0.1378 (4) | 0.0228 (2) | 0.0354 (8) | |
N2 | 0.6992 (2) | 0.4244 (4) | 0.1660 (2) | 0.0338 (8) | |
C5 | 0.5592 (3) | 0.3316 (4) | 0.0724 (3) | 0.0354 (9) | |
C16 | 0.8260 (3) | −0.0109 (5) | 0.0336 (3) | 0.0422 (10) | |
H16 | 0.7967 | −0.0561 | 0.0768 | 0.051* | |
C4 | 0.4563 (3) | 0.3177 (5) | 0.0396 (3) | 0.0490 (11) | |
H4 | 0.4057 | 0.3623 | 0.0668 | 0.059* | |
N6 | 0.8649 (3) | −0.0874 (4) | −0.0259 (2) | 0.0440 (9) | |
H6N | 0.8662 | −0.1853 | −0.0311 | 0.053* | |
N4 | 1.0755 (3) | 0.3503 (4) | 0.2121 (3) | 0.0520 (10) | |
H4N | 1.1378 | 0.3820 | 0.2139 | 0.062* | |
C6 | 0.5969 (3) | 0.4198 (4) | 0.1478 (2) | 0.0337 (9) | |
C15 | 0.9023 (4) | 0.0157 (5) | −0.0768 (3) | 0.0438 (11) | |
H15 | 0.9351 | −0.0055 | −0.1231 | 0.053* | |
C13 | 0.9979 (3) | 0.3740 (5) | 0.1492 (3) | 0.0474 (11) | |
H13 | 1.0039 | 0.4283 | 0.1007 | 0.057* | |
C12 | 1.0375 (4) | 0.2691 (6) | 0.2704 (3) | 0.0542 (12) | |
H12 | 1.0739 | 0.2366 | 0.3205 | 0.065* | |
C11 | 0.9379 (3) | 0.2420 (5) | 0.2447 (3) | 0.0463 (11) | |
H11 | 0.8932 | 0.1878 | 0.2739 | 0.056* | |
C7 | 0.5331 (3) | 0.4971 (5) | 0.1940 (3) | 0.0473 (11) | |
H7 | 0.4621 | 0.4904 | 0.1806 | 0.057* | |
C3 | 0.4301 (4) | 0.2394 (6) | −0.0318 (3) | 0.0550 (13) | |
H3 | 0.3613 | 0.2299 | −0.0539 | 0.066* | |
C1 | 0.6052 (3) | 0.1909 (5) | −0.0369 (3) | 0.0492 (11) | |
H1 | 0.6560 | 0.1469 | −0.0641 | 0.059* | |
C14 | 0.8826 (3) | 0.1543 (5) | −0.0471 (3) | 0.0413 (10) | |
H14 | 0.8988 | 0.2472 | −0.0702 | 0.050* | |
C2 | 0.5041 (4) | 0.1745 (6) | −0.0712 (3) | 0.0561 (12) | |
H2 | 0.4870 | 0.1201 | −0.1204 | 0.067* | |
C10 | 0.7403 (4) | 0.5111 (5) | 0.2303 (3) | 0.0473 (11) | |
H10 | 0.8115 | 0.5151 | 0.2429 | 0.057* | |
C9 | 0.6809 (4) | 0.5948 (6) | 0.2785 (3) | 0.0521 (12) | |
H9 | 0.7114 | 0.6559 | 0.3219 | 0.063* | |
C8 | 0.5759 (4) | 0.5859 (6) | 0.2611 (3) | 0.0568 (13) | |
H8 | 0.5340 | 0.6383 | 0.2935 | 0.068* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0465 (3) | 0.0403 (3) | 0.0764 (4) | 0.0040 (2) | 0.0209 (2) | 0.0122 (2) |
Br2 | 0.0267 (3) | 0.0645 (3) | 0.0571 (3) | 0.00046 (19) | 0.0031 (2) | 0.0073 (2) |
Cu1 | 0.0220 (3) | 0.0519 (4) | 0.0446 (3) | 0.0049 (2) | 0.0017 (2) | −0.0146 (2) |
N1 | 0.0275 (18) | 0.0396 (19) | 0.0400 (19) | 0.0012 (14) | 0.0006 (14) | 0.0009 (15) |
N3 | 0.0215 (17) | 0.044 (2) | 0.049 (2) | −0.0010 (14) | 0.0072 (15) | −0.0093 (16) |
N5 | 0.0274 (18) | 0.038 (2) | 0.0412 (19) | 0.0028 (14) | 0.0044 (15) | −0.0041 (15) |
N2 | 0.0261 (18) | 0.0371 (19) | 0.0388 (19) | 0.0012 (14) | 0.0060 (14) | −0.0039 (15) |
C5 | 0.025 (2) | 0.034 (2) | 0.048 (2) | 0.0025 (17) | 0.0060 (17) | 0.0101 (18) |
C16 | 0.035 (2) | 0.047 (3) | 0.044 (2) | −0.0013 (19) | 0.003 (2) | 0.005 (2) |
C4 | 0.025 (2) | 0.056 (3) | 0.066 (3) | 0.000 (2) | 0.003 (2) | 0.010 (2) |
N6 | 0.045 (2) | 0.034 (2) | 0.052 (2) | 0.0044 (16) | 0.0019 (17) | −0.0075 (17) |
N4 | 0.025 (2) | 0.054 (2) | 0.076 (3) | −0.0043 (17) | 0.0019 (19) | −0.014 (2) |
C6 | 0.027 (2) | 0.034 (2) | 0.041 (2) | 0.0024 (17) | 0.0077 (17) | 0.0077 (17) |
C15 | 0.044 (3) | 0.051 (3) | 0.037 (2) | 0.002 (2) | 0.008 (2) | −0.007 (2) |
C13 | 0.030 (2) | 0.051 (3) | 0.062 (3) | 0.001 (2) | 0.012 (2) | −0.001 (2) |
C12 | 0.043 (3) | 0.060 (3) | 0.055 (3) | 0.005 (2) | −0.012 (2) | −0.009 (2) |
C11 | 0.036 (2) | 0.055 (3) | 0.046 (3) | −0.003 (2) | −0.002 (2) | −0.001 (2) |
C7 | 0.032 (2) | 0.055 (3) | 0.058 (3) | 0.008 (2) | 0.016 (2) | 0.004 (2) |
C3 | 0.031 (2) | 0.062 (3) | 0.068 (3) | −0.007 (2) | −0.012 (2) | 0.011 (3) |
C1 | 0.040 (3) | 0.056 (3) | 0.048 (3) | 0.005 (2) | −0.006 (2) | −0.010 (2) |
C14 | 0.039 (2) | 0.043 (3) | 0.042 (2) | −0.0014 (19) | 0.0081 (19) | 0.0032 (19) |
C2 | 0.047 (3) | 0.062 (3) | 0.054 (3) | −0.002 (2) | −0.015 (2) | −0.007 (2) |
C10 | 0.033 (2) | 0.052 (3) | 0.057 (3) | 0.004 (2) | 0.006 (2) | −0.012 (2) |
C9 | 0.064 (3) | 0.048 (3) | 0.044 (3) | 0.001 (2) | 0.009 (2) | −0.013 (2) |
C8 | 0.055 (3) | 0.056 (3) | 0.064 (3) | 0.013 (2) | 0.027 (3) | −0.005 (3) |
Geometric parameters (Å, º) top
Br1—Cu1 | 2.8189 (10) | N4—C13 | 1.358 (6) |
Cu1—N5 | 1.991 (3) | N4—H4N | 0.8600 |
Cu1—N3 | 2.002 (3) | C6—C7 | 1.372 (6) |
Cu1—N2 | 2.013 (3) | C15—C14 | 1.340 (6) |
Cu1—N1 | 2.031 (3) | C15—H15 | 0.9300 |
N1—C1 | 1.328 (5) | C13—H13 | 0.9300 |
N1—C5 | 1.350 (5) | C12—C11 | 1.340 (6) |
N3—C13 | 1.320 (5) | C12—H12 | 0.9300 |
N3—C11 | 1.386 (6) | C11—H11 | 0.9300 |
N5—C16 | 1.317 (5) | C7—C8 | 1.392 (7) |
N5—C14 | 1.374 (5) | C7—H7 | 0.9300 |
N2—C6 | 1.335 (5) | C3—C2 | 1.355 (7) |
N2—C10 | 1.343 (6) | C3—H3 | 0.9300 |
C5—C4 | 1.389 (5) | C1—C2 | 1.376 (6) |
C5—C6 | 1.474 (6) | C1—H1 | 0.9300 |
C16—N6 | 1.328 (6) | C14—H14 | 0.9300 |
C16—H16 | 0.9300 | C2—H2 | 0.9300 |
C4—C3 | 1.349 (7) | C10—C9 | 1.383 (6) |
C4—H4 | 0.9300 | C10—H10 | 0.9300 |
N6—C15 | 1.356 (6) | C9—C8 | 1.371 (7) |
N6—H6N | 0.8600 | C9—H9 | 0.9300 |
N4—C12 | 1.330 (6) | C8—H8 | 0.9300 |
N5—Cu1—N3 | 90.96 (13) | N2—C6—C5 | 114.6 (3) |
N5—Cu1—N2 | 169.17 (13) | C7—C6—C5 | 123.1 (4) |
N3—Cu1—N2 | 95.70 (13) | C14—C15—N6 | 106.1 (4) |
N5—Cu1—N1 | 92.28 (13) | C14—C15—H15 | 126.9 |
N3—Cu1—N1 | 171.65 (13) | N6—C15—H15 | 126.9 |
N2—Cu1—N1 | 80.01 (13) | N3—C13—N4 | 110.0 (4) |
N5—Cu1—Br1 | 96.25 (10) | N3—C13—H13 | 125.0 |
N3—Cu1—Br1 | 93.75 (10) | N4—C13—H13 | 125.0 |
N2—Cu1—Br1 | 91.83 (10) | N4—C12—C11 | 108.2 (4) |
N1—Cu1—Br1 | 93.54 (9) | N4—C12—H12 | 125.9 |
C1—N1—C5 | 118.4 (4) | C11—C12—H12 | 125.9 |
C1—N1—Cu1 | 127.3 (3) | C12—C11—N3 | 108.4 (4) |
C5—N1—Cu1 | 114.3 (3) | C12—C11—H11 | 125.8 |
C13—N3—C11 | 105.8 (4) | N3—C11—H11 | 125.8 |
C13—N3—Cu1 | 127.1 (3) | C6—C7—C8 | 119.2 (4) |
C11—N3—Cu1 | 127.0 (3) | C6—C7—H7 | 120.4 |
C16—N5—C14 | 105.6 (4) | C8—C7—H7 | 120.4 |
C16—N5—Cu1 | 123.8 (3) | C4—C3—C2 | 119.9 (4) |
C14—N5—Cu1 | 130.4 (3) | C4—C3—H3 | 120.1 |
C6—N2—C10 | 118.5 (3) | C2—C3—H3 | 120.1 |
C6—N2—Cu1 | 115.7 (3) | N1—C1—C2 | 122.8 (4) |
C10—N2—Cu1 | 125.8 (3) | N1—C1—H1 | 118.6 |
N1—C5—C4 | 120.5 (4) | C2—C1—H1 | 118.6 |
N1—C5—C6 | 115.0 (3) | C15—C14—N5 | 109.4 (4) |
C4—C5—C6 | 124.5 (4) | C15—C14—H14 | 125.3 |
N5—C16—N6 | 110.6 (4) | N5—C14—H14 | 125.3 |
N5—C16—H16 | 124.7 | C3—C2—C1 | 118.6 (5) |
N6—C16—H16 | 124.7 | C3—C2—H2 | 120.7 |
C3—C4—C5 | 119.9 (4) | C1—C2—H2 | 120.7 |
C3—C4—H4 | 120.1 | N2—C10—C9 | 122.5 (4) |
C5—C4—H4 | 120.1 | N2—C10—H10 | 118.7 |
C16—N6—C15 | 108.2 (4) | C9—C10—H10 | 118.7 |
C16—N6—H6N | 125.9 | C8—C9—C10 | 118.6 (4) |
C15—N6—H6N | 125.9 | C8—C9—H9 | 120.7 |
C12—N4—C13 | 107.5 (4) | C10—C9—H9 | 120.7 |
C12—N4—H4N | 126.2 | C9—C8—C7 | 119.0 (4) |
C13—N4—H4N | 126.2 | C9—C8—H8 | 120.5 |
N2—C6—C7 | 122.2 (4) | C7—C8—H8 | 120.5 |
N5—Cu1—N1—C1 | −11.4 (4) | C14—N5—C16—N6 | −0.5 (5) |
N3—Cu1—N1—C1 | −124.2 (9) | Cu1—N5—C16—N6 | 175.8 (3) |
N2—Cu1—N1—C1 | 176.2 (4) | N1—C5—C4—C3 | −0.1 (6) |
Br1—Cu1—N1—C1 | 85.0 (4) | C6—C5—C4—C3 | 177.2 (4) |
N5—Cu1—N1—C5 | 166.7 (3) | N5—C16—N6—C15 | 1.1 (5) |
N3—Cu1—N1—C5 | 54.0 (10) | C10—N2—C6—C7 | −1.7 (6) |
N2—Cu1—N1—C5 | −5.6 (3) | Cu1—N2—C6—C7 | 177.3 (3) |
Br1—Cu1—N1—C5 | −96.8 (3) | C10—N2—C6—C5 | 175.4 (4) |
N5—Cu1—N3—C13 | 73.2 (4) | Cu1—N2—C6—C5 | −5.6 (4) |
N2—Cu1—N3—C13 | −115.3 (4) | N1—C5—C6—N2 | 0.8 (5) |
N1—Cu1—N3—C13 | −173.9 (8) | C4—C5—C6—N2 | −176.7 (4) |
Br1—Cu1—N3—C13 | −23.1 (3) | N1—C5—C6—C7 | 177.9 (4) |
N5—Cu1—N3—C11 | −101.6 (3) | C4—C5—C6—C7 | 0.4 (6) |
N2—Cu1—N3—C11 | 69.9 (3) | C16—N6—C15—C14 | −1.3 (5) |
N1—Cu1—N3—C11 | 11.2 (11) | C11—N3—C13—N4 | 0.4 (5) |
Br1—Cu1—N3—C11 | 162.1 (3) | Cu1—N3—C13—N4 | −175.3 (3) |
N3—Cu1—N5—C16 | 93.9 (3) | C12—N4—C13—N3 | −0.3 (5) |
N2—Cu1—N5—C16 | −34.1 (9) | C13—N4—C12—C11 | 0.1 (5) |
N1—Cu1—N5—C16 | −78.4 (3) | N4—C12—C11—N3 | 0.2 (5) |
Br1—Cu1—N5—C16 | −172.2 (3) | C13—N3—C11—C12 | −0.4 (5) |
N3—Cu1—N5—C14 | −90.8 (4) | Cu1—N3—C11—C12 | 175.4 (3) |
N2—Cu1—N5—C14 | 141.1 (6) | N2—C6—C7—C8 | 1.2 (7) |
N1—Cu1—N5—C14 | 96.9 (4) | C5—C6—C7—C8 | −175.7 (4) |
Br1—Cu1—N5—C14 | 3.1 (4) | C5—C4—C3—C2 | 0.0 (7) |
N5—Cu1—N2—C6 | −38.9 (8) | C5—N1—C1—C2 | −0.4 (7) |
N3—Cu1—N2—C6 | −166.6 (3) | Cu1—N1—C1—C2 | 177.7 (4) |
N1—Cu1—N2—C6 | 6.2 (3) | N6—C15—C14—N5 | 1.0 (5) |
Br1—Cu1—N2—C6 | 99.4 (3) | C16—N5—C14—C15 | −0.3 (5) |
N5—Cu1—N2—C10 | 140.0 (7) | Cu1—N5—C14—C15 | −176.3 (3) |
N3—Cu1—N2—C10 | 12.3 (4) | C4—C3—C2—C1 | −0.1 (7) |
N1—Cu1—N2—C10 | −174.9 (4) | N1—C1—C2—C3 | 0.3 (7) |
Br1—Cu1—N2—C10 | −81.7 (4) | C6—N2—C10—C9 | 0.4 (7) |
C1—N1—C5—C4 | 0.3 (6) | Cu1—N2—C10—C9 | −178.5 (4) |
Cu1—N1—C5—C4 | −178.1 (3) | N2—C10—C9—C8 | 1.5 (7) |
C1—N1—C5—C6 | −177.3 (4) | C10—C9—C8—C7 | −2.0 (7) |
Cu1—N1—C5—C6 | 4.3 (4) | C6—C7—C8—C9 | 0.8 (7) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···Br2i | 0.86 | 2.53 | 3.320 (4) | 152 |
N6—H6N···Br1ii | 0.86 | 2.45 | 3.254 (4) | 156 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, y−1, z. |