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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030284/ng6059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030284/ng6059Isup2.hkl
Contains datablock I

CCDC reference: 259078

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.034
  • wR factor = 0.108
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found




Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Br1 - Cu1 .. 51.61 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.53 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 N3 -CU1 -N1 -C1 -124.20 0.90 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 N3 -CU1 -N1 -C5 54.00 1.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N1 -CU1 -N3 -C13 -173.90 0.80 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 15 N1 -CU1 -N3 -C11 11.20 1.10 1.555 1.555 1.555 1.555
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.531 Tmax scaled 0.436 Tmin scaled 0.266
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 1 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 5 ALERT type 4 Improvement, methodology, query or suggestion

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].BrF(000) = 1012.0
Mr = 515.71Dx = 1.861 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3180 reflections
a = 13.121 (5) Åθ = 1.6–25.1°
b = 8.731 (3) ŵ = 5.54 mm1
c = 16.205 (6) ÅT = 298 K
β = 97.560 (6)°Prism, blue
V = 1840.2 (11) Å30.25 × 0.19 × 0.15 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
3180 independent reflections
Radiation source: fine-focus sealed tube2536 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1510
Tmin = 0.50, Tmax = 0.82k = 1010
8504 measured reflectionsl = 1819
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-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 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.38 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.81906 (4)0.54969 (5)0.00362 (3)0.05326 (18)
Br20.70482 (3)0.02184 (6)0.21618 (3)0.04965 (18)
Cu10.77800 (3)0.29466 (6)0.09347 (3)0.03975 (18)
N10.6332 (2)0.2670 (4)0.0334 (2)0.0360 (8)
N30.9127 (2)0.3087 (4)0.1670 (2)0.0380 (8)
N50.8347 (2)0.1378 (4)0.0228 (2)0.0354 (8)
N20.6992 (2)0.4244 (4)0.1660 (2)0.0338 (8)
C50.5592 (3)0.3316 (4)0.0724 (3)0.0354 (9)
C160.8260 (3)0.0109 (5)0.0336 (3)0.0422 (10)
H160.79670.05610.07680.051*
C40.4563 (3)0.3177 (5)0.0396 (3)0.0490 (11)
H40.40570.36230.06680.059*
N60.8649 (3)0.0874 (4)0.0259 (2)0.0440 (9)
H6N0.86620.18530.03110.053*
N41.0755 (3)0.3503 (4)0.2121 (3)0.0520 (10)
H4N1.13780.38200.21390.062*
C60.5969 (3)0.4198 (4)0.1478 (2)0.0337 (9)
C150.9023 (4)0.0157 (5)0.0768 (3)0.0438 (11)
H150.93510.00550.12310.053*
C130.9979 (3)0.3740 (5)0.1492 (3)0.0474 (11)
H131.00390.42830.10070.057*
C121.0375 (4)0.2691 (6)0.2704 (3)0.0542 (12)
H121.07390.23660.32050.065*
C110.9379 (3)0.2420 (5)0.2447 (3)0.0463 (11)
H110.89320.18780.27390.056*
C70.5331 (3)0.4971 (5)0.1940 (3)0.0473 (11)
H70.46210.49040.18060.057*
C30.4301 (4)0.2394 (6)0.0318 (3)0.0550 (13)
H30.36130.22990.05390.066*
C10.6052 (3)0.1909 (5)0.0369 (3)0.0492 (11)
H10.65600.14690.06410.059*
C140.8826 (3)0.1543 (5)0.0471 (3)0.0413 (10)
H140.89880.24720.07020.050*
C20.5041 (4)0.1745 (6)0.0712 (3)0.0561 (12)
H20.48700.12010.12040.067*
C100.7403 (4)0.5111 (5)0.2303 (3)0.0473 (11)
H100.81150.51510.24290.057*
C90.6809 (4)0.5948 (6)0.2785 (3)0.0521 (12)
H90.71140.65590.32190.063*
C80.5759 (4)0.5859 (6)0.2611 (3)0.0568 (13)
H80.53400.63830.29350.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0465 (3)0.0403 (3)0.0764 (4)0.0040 (2)0.0209 (2)0.0122 (2)
Br20.0267 (3)0.0645 (3)0.0571 (3)0.00046 (19)0.0031 (2)0.0073 (2)
Cu10.0220 (3)0.0519 (4)0.0446 (3)0.0049 (2)0.0017 (2)0.0146 (2)
N10.0275 (18)0.0396 (19)0.0400 (19)0.0012 (14)0.0006 (14)0.0009 (15)
N30.0215 (17)0.044 (2)0.049 (2)0.0010 (14)0.0072 (15)0.0093 (16)
N50.0274 (18)0.038 (2)0.0412 (19)0.0028 (14)0.0044 (15)0.0041 (15)
N20.0261 (18)0.0371 (19)0.0388 (19)0.0012 (14)0.0060 (14)0.0039 (15)
C50.025 (2)0.034 (2)0.048 (2)0.0025 (17)0.0060 (17)0.0101 (18)
C160.035 (2)0.047 (3)0.044 (2)0.0013 (19)0.003 (2)0.005 (2)
C40.025 (2)0.056 (3)0.066 (3)0.000 (2)0.003 (2)0.010 (2)
N60.045 (2)0.034 (2)0.052 (2)0.0044 (16)0.0019 (17)0.0075 (17)
N40.025 (2)0.054 (2)0.076 (3)0.0043 (17)0.0019 (19)0.014 (2)
C60.027 (2)0.034 (2)0.041 (2)0.0024 (17)0.0077 (17)0.0077 (17)
C150.044 (3)0.051 (3)0.037 (2)0.002 (2)0.008 (2)0.007 (2)
C130.030 (2)0.051 (3)0.062 (3)0.001 (2)0.012 (2)0.001 (2)
C120.043 (3)0.060 (3)0.055 (3)0.005 (2)0.012 (2)0.009 (2)
C110.036 (2)0.055 (3)0.046 (3)0.003 (2)0.002 (2)0.001 (2)
C70.032 (2)0.055 (3)0.058 (3)0.008 (2)0.016 (2)0.004 (2)
C30.031 (2)0.062 (3)0.068 (3)0.007 (2)0.012 (2)0.011 (3)
C10.040 (3)0.056 (3)0.048 (3)0.005 (2)0.006 (2)0.010 (2)
C140.039 (2)0.043 (3)0.042 (2)0.0014 (19)0.0081 (19)0.0032 (19)
C20.047 (3)0.062 (3)0.054 (3)0.002 (2)0.015 (2)0.007 (2)
C100.033 (2)0.052 (3)0.057 (3)0.004 (2)0.006 (2)0.012 (2)
C90.064 (3)0.048 (3)0.044 (3)0.001 (2)0.009 (2)0.013 (2)
C80.055 (3)0.056 (3)0.064 (3)0.013 (2)0.027 (3)0.005 (3)
Geometric parameters (Å, º) top
Br1—Cu12.8189 (10)N4—C131.358 (6)
Cu1—N51.991 (3)N4—H4N0.8600
Cu1—N32.002 (3)C6—C71.372 (6)
Cu1—N22.013 (3)C15—C141.340 (6)
Cu1—N12.031 (3)C15—H150.9300
N1—C11.328 (5)C13—H130.9300
N1—C51.350 (5)C12—C111.340 (6)
N3—C131.320 (5)C12—H120.9300
N3—C111.386 (6)C11—H110.9300
N5—C161.317 (5)C7—C81.392 (7)
N5—C141.374 (5)C7—H70.9300
N2—C61.335 (5)C3—C21.355 (7)
N2—C101.343 (6)C3—H30.9300
C5—C41.389 (5)C1—C21.376 (6)
C5—C61.474 (6)C1—H10.9300
C16—N61.328 (6)C14—H140.9300
C16—H160.9300C2—H20.9300
C4—C31.349 (7)C10—C91.383 (6)
C4—H40.9300C10—H100.9300
N6—C151.356 (6)C9—C81.371 (7)
N6—H6N0.8600C9—H90.9300
N4—C121.330 (6)C8—H80.9300
N5—Cu1—N390.96 (13)N2—C6—C5114.6 (3)
N5—Cu1—N2169.17 (13)C7—C6—C5123.1 (4)
N3—Cu1—N295.70 (13)C14—C15—N6106.1 (4)
N5—Cu1—N192.28 (13)C14—C15—H15126.9
N3—Cu1—N1171.65 (13)N6—C15—H15126.9
N2—Cu1—N180.01 (13)N3—C13—N4110.0 (4)
N5—Cu1—Br196.25 (10)N3—C13—H13125.0
N3—Cu1—Br193.75 (10)N4—C13—H13125.0
N2—Cu1—Br191.83 (10)N4—C12—C11108.2 (4)
N1—Cu1—Br193.54 (9)N4—C12—H12125.9
C1—N1—C5118.4 (4)C11—C12—H12125.9
C1—N1—Cu1127.3 (3)C12—C11—N3108.4 (4)
C5—N1—Cu1114.3 (3)C12—C11—H11125.8
C13—N3—C11105.8 (4)N3—C11—H11125.8
C13—N3—Cu1127.1 (3)C6—C7—C8119.2 (4)
C11—N3—Cu1127.0 (3)C6—C7—H7120.4
C16—N5—C14105.6 (4)C8—C7—H7120.4
C16—N5—Cu1123.8 (3)C4—C3—C2119.9 (4)
C14—N5—Cu1130.4 (3)C4—C3—H3120.1
C6—N2—C10118.5 (3)C2—C3—H3120.1
C6—N2—Cu1115.7 (3)N1—C1—C2122.8 (4)
C10—N2—Cu1125.8 (3)N1—C1—H1118.6
N1—C5—C4120.5 (4)C2—C1—H1118.6
N1—C5—C6115.0 (3)C15—C14—N5109.4 (4)
C4—C5—C6124.5 (4)C15—C14—H14125.3
N5—C16—N6110.6 (4)N5—C14—H14125.3
N5—C16—H16124.7C3—C2—C1118.6 (5)
N6—C16—H16124.7C3—C2—H2120.7
C3—C4—C5119.9 (4)C1—C2—H2120.7
C3—C4—H4120.1N2—C10—C9122.5 (4)
C5—C4—H4120.1N2—C10—H10118.7
C16—N6—C15108.2 (4)C9—C10—H10118.7
C16—N6—H6N125.9C8—C9—C10118.6 (4)
C15—N6—H6N125.9C8—C9—H9120.7
C12—N4—C13107.5 (4)C10—C9—H9120.7
C12—N4—H4N126.2C9—C8—C7119.0 (4)
C13—N4—H4N126.2C9—C8—H8120.5
N2—C6—C7122.2 (4)C7—C8—H8120.5
N5—Cu1—N1—C111.4 (4)C14—N5—C16—N60.5 (5)
N3—Cu1—N1—C1124.2 (9)Cu1—N5—C16—N6175.8 (3)
N2—Cu1—N1—C1176.2 (4)N1—C5—C4—C30.1 (6)
Br1—Cu1—N1—C185.0 (4)C6—C5—C4—C3177.2 (4)
N5—Cu1—N1—C5166.7 (3)N5—C16—N6—C151.1 (5)
N3—Cu1—N1—C554.0 (10)C10—N2—C6—C71.7 (6)
N2—Cu1—N1—C55.6 (3)Cu1—N2—C6—C7177.3 (3)
Br1—Cu1—N1—C596.8 (3)C10—N2—C6—C5175.4 (4)
N5—Cu1—N3—C1373.2 (4)Cu1—N2—C6—C55.6 (4)
N2—Cu1—N3—C13115.3 (4)N1—C5—C6—N20.8 (5)
N1—Cu1—N3—C13173.9 (8)C4—C5—C6—N2176.7 (4)
Br1—Cu1—N3—C1323.1 (3)N1—C5—C6—C7177.9 (4)
N5—Cu1—N3—C11101.6 (3)C4—C5—C6—C70.4 (6)
N2—Cu1—N3—C1169.9 (3)C16—N6—C15—C141.3 (5)
N1—Cu1—N3—C1111.2 (11)C11—N3—C13—N40.4 (5)
Br1—Cu1—N3—C11162.1 (3)Cu1—N3—C13—N4175.3 (3)
N3—Cu1—N5—C1693.9 (3)C12—N4—C13—N30.3 (5)
N2—Cu1—N5—C1634.1 (9)C13—N4—C12—C110.1 (5)
N1—Cu1—N5—C1678.4 (3)N4—C12—C11—N30.2 (5)
Br1—Cu1—N5—C16172.2 (3)C13—N3—C11—C120.4 (5)
N3—Cu1—N5—C1490.8 (4)Cu1—N3—C11—C12175.4 (3)
N2—Cu1—N5—C14141.1 (6)N2—C6—C7—C81.2 (7)
N1—Cu1—N5—C1496.9 (4)C5—C6—C7—C8175.7 (4)
Br1—Cu1—N5—C143.1 (4)C5—C4—C3—C20.0 (7)
N5—Cu1—N2—C638.9 (8)C5—N1—C1—C20.4 (7)
N3—Cu1—N2—C6166.6 (3)Cu1—N1—C1—C2177.7 (4)
N1—Cu1—N2—C66.2 (3)N6—C15—C14—N51.0 (5)
Br1—Cu1—N2—C699.4 (3)C16—N5—C14—C150.3 (5)
N5—Cu1—N2—C10140.0 (7)Cu1—N5—C14—C15176.3 (3)
N3—Cu1—N2—C1012.3 (4)C4—C3—C2—C10.1 (7)
N1—Cu1—N2—C10174.9 (4)N1—C1—C2—C30.3 (7)
Br1—Cu1—N2—C1081.7 (4)C6—N2—C10—C90.4 (7)
C1—N1—C5—C40.3 (6)Cu1—N2—C10—C9178.5 (4)
Cu1—N1—C5—C4178.1 (3)N2—C10—C9—C81.5 (7)
C1—N1—C5—C6177.3 (4)C10—C9—C8—C72.0 (7)
Cu1—N1—C5—C64.3 (4)C6—C7—C8—C90.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···Br2i0.862.533.320 (4)152
N6—H6N···Br1ii0.862.453.254 (4)156
Symmetry codes: (i) x+2, y+1/2, z+1/2; (ii) x, y1, z.
 

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