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metal-organic compounds
The Cu atom in the 1/1 adduct of copper(II) diiodide with 4′-phenyl-2,2′:6′,2′′-terpyridine, [CuI2(C21H15N3)], exists in a square-pyramidal environment. The Cu—Iaxial bond [2.7872 (9) Å] is significantly longer than the Cu—Ibasal bond [2.5394 (8) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017672/bt6490sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017672/bt6490Isup2.hkl |
CCDC reference: 248755
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.009 Å
- R factor = 0.040
- wR factor = 0.111
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) I1 - Cu1 .. 10.30 su
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 0 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: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[CuI2(C21H15N3)] | F(000) = 2376 |
Mr = 626.70 | Dx = 2.086 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2748 reflections |
a = 13.855 (1) Å | θ = 2.7–23.2° |
b = 14.995 (1) Å | µ = 4.20 mm−1 |
c = 19.245 (1) Å | T = 295 K |
β = 93.571 (1)° | Prism, black |
V = 3990.6 (5) Å3 | 0.19 × 0.18 × 0.12 mm |
Z = 8 |
Data collection top
Bruker APEX area-detector diffractometer | 3513 independent reflections |
Radiation source: fine-focus sealed tube | 2977 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −16→16 |
Tmin = 0.454, Tmax = 0.604 | k = −14→17 |
10302 measured reflections | l = −22→17 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0608P)2 + 14.3913P] where P = (Fo2 + 2Fc2)/3 |
3513 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 1.18 e Å−3 |
0 restraints | Δρmin = −0.87 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
I1 | 0.85824 (3) | 0.58227 (3) | 0.32953 (3) | 0.0525 (2) | |
I2 | 0.61350 (3) | 0.53073 (3) | 0.44392 (2) | 0.0507 (2) | |
Cu1 | 0.65787 (5) | 0.59887 (5) | 0.32940 (4) | 0.0350 (2) | |
N1 | 0.6419 (4) | 0.7320 (3) | 0.3567 (2) | 0.038 (1) | |
N2 | 0.6300 (3) | 0.6537 (3) | 0.2379 (2) | 0.032 (1) | |
N3 | 0.6366 (4) | 0.4874 (3) | 0.2669 (2) | 0.034 (1) | |
C1 | 0.6412 (5) | 0.7664 (5) | 0.4200 (3) | 0.049 (2) | |
C2 | 0.6217 (6) | 0.8542 (5) | 0.4327 (4) | 0.057 (2) | |
C3 | 0.6023 (6) | 0.9089 (5) | 0.3768 (4) | 0.055 (2) | |
C4 | 0.6071 (5) | 0.8763 (4) | 0.3100 (3) | 0.041 (1) | |
C5 | 0.6259 (4) | 0.7877 (4) | 0.3016 (3) | 0.035 (1) | |
C6 | 0.6265 (4) | 0.7422 (4) | 0.2333 (3) | 0.032 (1) | |
C7 | 0.6223 (4) | 0.7848 (4) | 0.1687 (3) | 0.036 (1) | |
C8 | 0.6205 (4) | 0.7318 (4) | 0.1084 (3) | 0.035 (1) | |
C9 | 0.6205 (4) | 0.6388 (4) | 0.1163 (3) | 0.036 (1) | |
C10 | 0.6267 (4) | 0.6017 (4) | 0.1814 (3) | 0.032 (1) | |
C11 | 0.6303 (4) | 0.5055 (4) | 0.1979 (3) | 0.032 (1) | |
C12 | 0.6283 (5) | 0.4388 (4) | 0.1487 (3) | 0.041 (2) | |
C13 | 0.6318 (5) | 0.3512 (4) | 0.1704 (3) | 0.043 (2) | |
C14 | 0.6376 (5) | 0.3327 (4) | 0.2402 (3) | 0.043 (2) | |
C15 | 0.6400 (5) | 0.4022 (4) | 0.2872 (3) | 0.043 (2) | |
C16 | 0.6206 (4) | 0.7729 (4) | 0.0387 (3) | 0.035 (1) | |
C17 | 0.6671 (5) | 0.8541 (4) | 0.0294 (3) | 0.044 (2) | |
C18 | 0.6706 (5) | 0.8905 (5) | −0.0364 (3) | 0.049 (2) | |
C19 | 0.6256 (5) | 0.8483 (5) | −0.0926 (3) | 0.046 (2) | |
C20 | 0.5782 (5) | 0.7689 (4) | −0.0842 (3) | 0.044 (2) | |
C21 | 0.5761 (4) | 0.7317 (4) | −0.0192 (3) | 0.042 (1) | |
H1 | 0.6548 | 0.7290 | 0.4578 | 0.059* | |
H2 | 0.6216 | 0.8759 | 0.4779 | 0.068* | |
H3 | 0.5858 | 0.9682 | 0.3837 | 0.066* | |
H4 | 0.5979 | 0.9138 | 0.2716 | 0.050* | |
H7 | 0.6206 | 0.8467 | 0.1657 | 0.043* | |
H9 | 0.6163 | 0.6023 | 0.0772 | 0.043* | |
H12 | 0.6246 | 0.4526 | 0.1015 | 0.049* | |
H13 | 0.6302 | 0.3052 | 0.1379 | 0.051* | |
H14 | 0.6398 | 0.2739 | 0.2557 | 0.051* | |
H15 | 0.6441 | 0.3893 | 0.3346 | 0.052* | |
H17 | 0.6960 | 0.8839 | 0.0676 | 0.053* | |
H18 | 0.7035 | 0.9437 | −0.0425 | 0.059* | |
H19 | 0.6271 | 0.8735 | −0.1366 | 0.056* | |
H20 | 0.5476 | 0.7405 | −0.1225 | 0.052* | |
H21 | 0.5441 | 0.6778 | −0.0140 | 0.050* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0400 (3) | 0.0397 (3) | 0.0775 (4) | −0.0009 (2) | 0.0014 (2) | −0.0018 (2) |
I2 | 0.0680 (3) | 0.0470 (3) | 0.0378 (3) | 0.0066 (2) | 0.0098 (2) | 0.00964 (18) |
Cu1 | 0.0453 (4) | 0.0283 (4) | 0.0309 (4) | −0.0001 (3) | −0.0007 (3) | 0.0005 (3) |
N1 | 0.043 (3) | 0.036 (3) | 0.033 (3) | −0.001 (2) | 0.001 (2) | 0.000 (2) |
N2 | 0.036 (3) | 0.027 (3) | 0.035 (3) | 0.001 (2) | 0.002 (2) | −0.002 (2) |
N3 | 0.042 (3) | 0.028 (3) | 0.032 (3) | 0.000 (2) | −0.001 (2) | 0.001 (2) |
C1 | 0.063 (4) | 0.045 (4) | 0.039 (4) | −0.003 (3) | 0.001 (3) | −0.001 (3) |
C2 | 0.085 (5) | 0.038 (4) | 0.048 (4) | −0.010 (4) | 0.008 (4) | −0.017 (3) |
C3 | 0.068 (5) | 0.033 (4) | 0.064 (5) | −0.003 (3) | 0.002 (4) | −0.018 (3) |
C4 | 0.050 (4) | 0.028 (3) | 0.045 (4) | −0.001 (3) | −0.002 (3) | −0.001 (3) |
C5 | 0.033 (3) | 0.031 (3) | 0.039 (3) | −0.006 (2) | 0.001 (2) | −0.001 (3) |
C6 | 0.033 (3) | 0.025 (3) | 0.037 (3) | −0.002 (2) | 0.000 (2) | −0.003 (2) |
C7 | 0.038 (3) | 0.028 (3) | 0.041 (3) | −0.003 (2) | 0.000 (3) | 0.003 (2) |
C8 | 0.032 (3) | 0.030 (3) | 0.042 (3) | −0.005 (2) | −0.001 (2) | 0.005 (2) |
C9 | 0.035 (3) | 0.031 (3) | 0.041 (3) | −0.004 (2) | 0.003 (3) | −0.001 (3) |
C10 | 0.034 (3) | 0.027 (3) | 0.035 (3) | 0.000 (2) | 0.003 (2) | 0.000 (2) |
C11 | 0.032 (3) | 0.029 (3) | 0.035 (3) | 0.000 (2) | −0.001 (2) | 0.001 (2) |
C12 | 0.051 (4) | 0.033 (3) | 0.040 (3) | −0.001 (3) | −0.001 (3) | −0.005 (3) |
C13 | 0.053 (4) | 0.029 (3) | 0.046 (4) | 0.004 (3) | −0.001 (3) | −0.005 (3) |
C14 | 0.051 (4) | 0.024 (3) | 0.053 (4) | 0.003 (3) | −0.002 (3) | 0.002 (3) |
C15 | 0.058 (4) | 0.029 (3) | 0.042 (4) | 0.002 (3) | −0.003 (3) | 0.006 (3) |
C16 | 0.032 (3) | 0.036 (3) | 0.036 (3) | 0.002 (3) | −0.003 (2) | 0.005 (3) |
C17 | 0.048 (4) | 0.037 (4) | 0.047 (4) | −0.005 (3) | −0.006 (3) | 0.006 (3) |
C18 | 0.051 (4) | 0.043 (4) | 0.051 (4) | −0.009 (3) | −0.008 (3) | 0.013 (3) |
C19 | 0.051 (4) | 0.048 (4) | 0.040 (4) | 0.010 (3) | 0.001 (3) | 0.012 (3) |
C20 | 0.056 (4) | 0.037 (4) | 0.036 (3) | 0.005 (3) | −0.004 (3) | −0.002 (3) |
C21 | 0.045 (4) | 0.032 (3) | 0.047 (4) | 0.000 (3) | 0.003 (3) | 0.000 (3) |
Geometric parameters (Å, º) top
I1—Cu1 | 2.7872 (9) | C13—C14 | 1.370 (9) |
I2—Cu1 | 2.5394 (8) | C14—C15 | 1.379 (9) |
Cu1—N1 | 2.079 (5) | C16—C21 | 1.386 (8) |
Cu1—N2 | 1.959 (5) | C16—C17 | 1.394 (8) |
Cu1—N3 | 2.069 (5) | C17—C18 | 1.381 (9) |
N1—C1 | 1.323 (8) | C18—C19 | 1.369 (9) |
N1—C5 | 1.357 (7) | C19—C20 | 1.374 (9) |
N2—C6 | 1.331 (7) | C20—C21 | 1.371 (9) |
N2—C10 | 1.337 (7) | C1—H1 | 0.93 |
N3—C15 | 1.336 (7) | C2—H2 | 0.93 |
N3—C11 | 1.354 (7) | C3—H3 | 0.93 |
C1—C2 | 1.37 (1) | C4—H4 | 0.93 |
C2—C3 | 1.37 (1) | C7—H7 | 0.93 |
C3—C4 | 1.381 (9) | C9—H9 | 0.93 |
C4—C5 | 1.365 (8) | C12—H12 | 0.93 |
C5—C6 | 1.480 (8) | C13—H13 | 0.93 |
C6—C7 | 1.395 (8) | C14—H14 | 0.93 |
C7—C8 | 1.406 (8) | C15—H15 | 0.93 |
C8—C9 | 1.402 (8) | C17—H17 | 0.93 |
C8—C16 | 1.477 (8) | C18—H18 | 0.93 |
C9—C10 | 1.369 (8) | C19—H19 | 0.93 |
C10—C11 | 1.476 (8) | C20—H20 | 0.93 |
C11—C12 | 1.377 (8) | C21—H21 | 0.93 |
C12—C13 | 1.377 (9) | ||
N1—Cu1—N2 | 78.8 (2) | C14—C13—C12 | 119.3 (6) |
N1—Cu1—N3 | 155.3 (2) | C13—C14—C15 | 119.2 (6) |
N1—Cu1—I1 | 102.0 (1) | N3—C15—C14 | 122.1 (6) |
N1—Cu1—I2 | 97.6 (1) | C21—C16—C17 | 118.2 (6) |
N2—Cu1—N3 | 78.7 (2) | C21—C16—C8 | 121.3 (5) |
N2—Cu1—I1 | 100.3 (1) | C17—C16—C8 | 120.5 (5) |
N2—Cu1—I2 | 154.7 (1) | C18—C17—C16 | 120.4 (6) |
N3—Cu1—I1 | 92.0 (1) | C19—C18—C17 | 120.1 (6) |
N3—Cu1—I2 | 98.4 (1) | C18—C19—C20 | 120.3 (6) |
I1—Cu1—I2 | 104.96 (3) | C21—C20—C19 | 119.9 (6) |
C1—N1—C5 | 118.0 (5) | C20—C21—C16 | 121.2 (6) |
C1—N1—Cu1 | 127.9 (4) | N1—C1—H1 | 118.2 |
C5—N1—Cu1 | 114.1 (4) | C2—C1—H1 | 118.2 |
C6—N2—C10 | 121.9 (5) | C1—C2—H2 | 121.1 |
C6—N2—Cu1 | 118.9 (4) | C3—C2—H2 | 121.1 |
C10—N2—Cu1 | 118.8 (4) | C2—C3—H3 | 119.9 |
C15—N3—C11 | 118.5 (5) | C4—C3—H3 | 119.9 |
C15—N3—Cu1 | 127.0 (4) | C5—C4—H4 | 120.8 |
C11—N3—Cu1 | 114.0 (4) | C3—C4—H4 | 120.8 |
N1—C1—C2 | 123.6 (7) | C6—C7—H7 | 120.8 |
C1—C2—C3 | 117.9 (6) | C8—C7—H7 | 120.8 |
C2—C3—C4 | 120.1 (6) | C10—C9—H9 | 119.9 |
C5—C4—C3 | 118.4 (6) | C8—C9—H9 | 119.9 |
C4—C5—N1 | 121.9 (6) | C11—C12—H12 | 120.5 |
C4—C5—C6 | 124.4 (5) | C13—C12—H12 | 120.5 |
N1—C5—C6 | 113.6 (5) | C14—C13—H13 | 120.3 |
N2—C6—C7 | 121.0 (5) | C12—C13—H13 | 120.3 |
N2—C6—C5 | 113.7 (5) | C13—C14—H14 | 120.4 |
C7—C6—C5 | 125.3 (5) | C15—C14—H14 | 120.4 |
C6—C7—C8 | 118.3 (5) | N3—C15—H15 | 118.9 |
C7—C8—C9 | 118.2 (5) | C14—C15—H15 | 118.9 |
C7—C8—C16 | 120.9 (5) | C18—C17—H17 | 119.8 |
C9—C8—C16 | 120.9 (5) | C16—C17—H17 | 119.8 |
C10—C9—C8 | 120.2 (6) | C19—C18—H18 | 120.0 |
N2—C10—C9 | 120.3 (5) | C17—C18—H18 | 120.0 |
N2—C10—C11 | 113.3 (5) | C18—C19—H19 | 119.8 |
C9—C10—C11 | 126.4 (5) | C20—C19—H19 | 119.8 |
N3—C11—C12 | 121.8 (5) | C21—C20—H20 | 120.1 |
N3—C11—C10 | 113.9 (5) | C19—C20—H20 | 120.1 |
C12—C11—C10 | 124.3 (5) | C20—C21—H21 | 119.4 |
C11—C12—C13 | 119.0 (6) | C16—C21—H21 | 119.4 |
N2—Cu1—N1—C1 | 173.9 (6) | C4—C5—C6—C7 | 10.0 (9) |
N3—Cu1—N1—C1 | 149.2 (5) | N1—C5—C6—C7 | −172.8 (5) |
I2—Cu1—N1—C1 | 19.3 (5) | N2—C6—C7—C8 | 0.8 (9) |
I1—Cu1—N1—C1 | −87.8 (5) | C5—C6—C7—C8 | −178.1 (5) |
N2—Cu1—N1—C5 | −2.8 (4) | C6—C7—C8—C9 | 1.7 (8) |
N3—Cu1—N1—C5 | −27.5 (7) | C6—C7—C8—C16 | −177.2 (5) |
I2—Cu1—N1—C5 | −157.4 (4) | C7—C8—C9—C10 | −3.1 (8) |
I1—Cu1—N1—C5 | 95.5 (4) | C16—C8—C9—C10 | 175.8 (5) |
N3—Cu1—N2—C6 | 177.7 (5) | C6—N2—C10—C9 | 0.7 (8) |
N1—Cu1—N2—C6 | 8.0 (4) | Cu1—N2—C10—C9 | −171.1 (4) |
I2—Cu1—N2—C6 | 92.0 (5) | C6—N2—C10—C11 | −179.2 (5) |
I1—Cu1—N2—C6 | −92.3 (4) | Cu1—N2—C10—C11 | 8.9 (7) |
N3—Cu1—N2—C10 | −10.2 (4) | C8—C9—C10—N2 | 1.9 (8) |
N1—Cu1—N2—C10 | −180.0 (5) | C8—C9—C10—C11 | −178.2 (6) |
I2—Cu1—N2—C10 | −95.9 (5) | C15—N3—C11—C12 | −0.7 (8) |
I1—Cu1—N2—C10 | 79.7 (4) | Cu1—N3—C11—C12 | 171.8 (5) |
N2—Cu1—N3—C15 | −178.8 (6) | C15—N3—C11—C10 | 179.8 (5) |
N1—Cu1—N3—C15 | −154.1 (5) | Cu1—N3—C11—C10 | −7.7 (6) |
I2—Cu1—N3—C15 | −24.3 (5) | N2—C10—C11—N3 | −0.3 (7) |
I1—Cu1—N3—C15 | 81.1 (5) | C9—C10—C11—N3 | 179.8 (5) |
N2—Cu1—N3—C11 | 9.6 (4) | N2—C10—C11—C12 | −179.7 (5) |
N1—Cu1—N3—C11 | 34.2 (7) | C9—C10—C11—C12 | 0 (1) |
I2—Cu1—N3—C11 | 164.0 (4) | N3—C11—C12—C13 | 0.7 (9) |
I1—Cu1—N3—C11 | −90.6 (4) | C10—C11—C12—C13 | −179.8 (6) |
C5—N1—C1—C2 | 3 (1) | C11—C12—C13—C14 | 0 (1) |
Cu1—N1—C1—C2 | −174.0 (6) | C12—C13—C14—C15 | 0 (1) |
N1—C1—C2—C3 | 0 (1) | C11—N3—C15—C14 | 0.2 (9) |
C1—C2—C3—C4 | −3 (1) | Cu1—N3—C15—C14 | −171.1 (5) |
C2—C3—C4—C5 | 4 (1) | C13—C14—C15—N3 | 0 (1) |
C3—C4—C5—N1 | −1.5 (9) | C7—C8—C16—C21 | −149.8 (6) |
C3—C4—C5—C6 | 175.5 (6) | C9—C8—C16—C21 | 31.4 (9) |
C1—N1—C5—C4 | −1.6 (9) | C7—C8—C16—C17 | 31.2 (8) |
Cu1—N1—C5—C4 | 175.4 (5) | C9—C8—C16—C17 | −147.6 (6) |
C1—N1—C5—C6 | −179.0 (5) | C21—C16—C17—C18 | −1.8 (9) |
Cu1—N1—C5—C6 | −1.9 (6) | C8—C16—C17—C18 | 177.3 (6) |
C10—N2—C6—C7 | −2.1 (9) | C16—C17—C18—C19 | 2 (1) |
Cu1—N2—C6—C7 | 169.7 (4) | C17—C18—C19—C20 | −1 (1) |
C10—N2—C6—C5 | 177.0 (5) | C18—C19—C20—C21 | 0 (1) |
Cu1—N2—C6—C5 | −11.2 (6) | C19—C20—C21—C16 | 0 (1) |
C4—C5—C6—N2 | −169.1 (6) | C17—C16—C21—C20 | 0.6 (9) |
N1—C5—C6—N2 | 8.2 (7) | C8—C16—C21—C20 | −178.4 (6) |
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