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The title compound, {[CuI(bpe)]·0.25(bpe)}n, was synthesized similarly to (CuI)2(bpe) [Neal et al. (2019). IUCrData, 4, x190122] with red crystals grown from aceto­nitrile solutions of CuI and the bpe ligand [bpe = 1,2-bis­(pyridin-4-yl)ethene, C12H10N2]. The structure of the title compound is a type 1 complex in the Graham nomenclature [Graham et al. (2000). Inorg. Chem. 39, 5121–5132], having rhombic dimers of Cu2I2 that are bridged by two bpe ligands, to form oligomeric ribbons arranged as stairsteps. The step height is 2.8072 (11) Å, which is the Cu—Ii distance of the dimer [symmetry code (i): 1 − x, 2 − y, 1 − z]. The resulting polymer displays a two-dimensional honeycomb framework along the (01\overline1) plane, and disordered free bpe mol­ecules fill the voids in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314620009980/bh4052sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314620009980/bh4052Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2414314620009980/bh4052Isup3.mol
Supplementary material

CCDC reference: 2017730

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.035
  • wR factor = 0.091
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT031_ALERT_4_B Refined Extinction Parameter Within Range ...... 2.250 Sigma
Alert level C PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of Cu1 Check PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C8 Check PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C9 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of N2 Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C10 Check PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors of C16 Check PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.5 Note PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.3 Note PLAT260_ALERT_2_C Large Average Ueq of Residue Including N17 0.205 Check PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00933 Ang. PLAT411_ALERT_2_C Short Inter H...H Contact H9 ..H13 . 2.12 Ang. 1-x,1-y,2-z = 2_667 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.597 18 Report PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 6 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 6 Report PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension 2 Info PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ... 0.50 Check PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 8 Report PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records 1 Report PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records 1 Report PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 1 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) I1 --Cu1 . 27.0 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) I1 --Cu1_b . 49.4 s.u. PLAT300_ALERT_4_G Atom Site Occupancy of N17 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C13 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C14 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C15 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C18 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H13 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H15 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H16 Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H18 Constrained at 0.5 Check PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 2 ) 71% Note PLAT432_ALERT_2_G Short Inter X...Y Contact C13 ..C13 1.30 Ang. 2-x,1-y,2-z = 2_767 Check PLAT432_ALERT_2_G Short Inter X...Y Contact C13 ..C14 2.43 Ang. 2-x,1-y,2-z = 2_767 Check PLAT432_ALERT_2_G Short Inter X...Y Contact C13 ..C15 3.10 Ang. 2-x,1-y,2-z = 2_767 Check PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.19 Ratio PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle(s) in CIF . # 65 Check C16 -C15 -H 1.555 1.555 2.667 44.90 Deg. PLAT780_ALERT_1_G Coordinates do not Form a Properly Connected Set Please Do ! PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 87 Note PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 47% Note PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 13 ALERT level C = Check. Ensure it is not caused by an omission or oversight 34 ALERT level G = General information/check it is not something unexpected 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 18 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 20 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[[[µ-trans-1,2-bis(pyridin-4-yl)ethene-κ2N:N']-µ-iodido-copper(I)]–trans-1,2-bis(pyridin-4-yl)ethene (1/0.25)] top
Crystal data top
[CuI(C12H10N2)·0.25C12H10N2Z = 2
Mr = 418.21F(000) = 404
Triclinic, P1Dx = 1.846 Mg m3
a = 7.9004 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.4260 (3) ÅCell parameters from 6736 reflections
c = 10.5078 (3) Åθ = 2.1–24.7°
α = 99.903 (2)°µ = 3.49 mm1
β = 104.930 (2)°T = 293 K
γ = 110.061 (3)°Block, red
V = 752.55 (4) Å30.14 × 0.10 × 0.06 mm
Data collection top
Rigaku XtaLAB Mini II
diffractometer
2683 independent reflections
Radiation source: fine-focus sealed X-ray tube, Rigaku (Mo) X-ray Source2021 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1Rint = 0.033
ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan
(CrysAlis Pro; Rigaku OD, 2019)
h = 99
Tmin = 0.838, Tmax = 1.000k = 1212
16024 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0389P)2 + 1.4132P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2683 reflectionsΔρmax = 0.60 e Å3
200 parametersΔρmin = 1.01 e Å3
87 restraintsExtinction correction: SHELXL-2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0018 (8)
Primary atom site location: dual
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.26536 (6)0.84672 (5)0.33204 (4)0.06679 (19)
Cu10.47272 (12)0.86742 (10)0.58757 (8)0.0777 (3)
N10.6174 (6)0.7452 (5)0.5719 (5)0.0605 (12)
N20.3214 (6)0.8771 (5)0.7122 (4)0.0515 (10)
C10.6526 (9)0.6715 (7)0.6588 (6)0.0683 (16)
H10.6034380.6748850.7301520.082*
C20.7563 (8)0.5909 (6)0.6505 (6)0.0657 (16)
H20.7737350.5403430.7139490.079*
C30.8346 (8)0.5847 (6)0.5482 (6)0.0572 (14)
C40.7964 (9)0.6579 (7)0.4552 (7)0.0743 (18)
H40.8436180.6555220.3827770.089*
C50.6875 (9)0.7351 (7)0.4697 (7)0.0752 (18)
H50.6617500.7825440.4047760.090*
C60.9505 (8)0.5005 (6)0.5415 (6)0.0614 (15)
H60.9537050.4437930.6005780.074*
C70.0594 (8)0.9694 (6)1.0045 (5)0.0578 (14)
H70.0934270.9429771.0842130.069*
C80.3474 (10)0.8408 (8)0.8268 (6)0.090 (2)
H80.4270470.7929990.8444600.108*
C90.2652 (10)0.8686 (8)0.9223 (6)0.089 (2)
H90.2908390.8401431.0018010.107*
C100.1457 (7)0.9378 (5)0.9018 (5)0.0470 (12)
C110.1145 (8)0.9735 (6)0.7811 (6)0.0625 (15)
H110.0340061.0200250.7602520.075*
C120.2020 (8)0.9406 (6)0.6906 (6)0.0643 (16)
H120.1754980.9645830.6086840.077*
C130.9182 (15)0.4586 (15)1.002 (3)0.207 (11)0.5
H130.9011390.3637301.0056120.248*0.5
C140.7563 (17)0.4951 (16)0.9907 (15)0.157 (8)0.5
C150.7591 (17)0.6220 (15)1.0534 (17)0.173 (9)0.5
H150.8733660.7088591.0900840.207*0.5
C160.5871 (15)0.6190 (9)1.0550 (15)0.265 (11)
H160.5873570.7073401.1004020.318*0.5
H0.2981370.2959300.9241520.318*0.5
N170.4132 (18)0.5088 (14)1.002 (3)0.268 (16)0.5
C180.5760 (17)0.3832 (16)0.926 (2)0.161 (8)0.5
H180.5681670.3002600.8638810.193*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0821 (3)0.0961 (3)0.0635 (3)0.0621 (3)0.0395 (2)0.0464 (2)
Cu10.0954 (6)0.1227 (7)0.0726 (5)0.0872 (6)0.0535 (4)0.0401 (5)
N10.068 (3)0.084 (3)0.065 (3)0.056 (3)0.039 (2)0.030 (2)
N20.061 (3)0.068 (3)0.053 (2)0.045 (2)0.033 (2)0.025 (2)
C10.081 (4)0.100 (5)0.067 (4)0.067 (4)0.043 (3)0.039 (3)
C20.075 (4)0.084 (4)0.076 (4)0.057 (4)0.041 (3)0.039 (3)
C30.055 (3)0.064 (3)0.077 (4)0.043 (3)0.032 (3)0.028 (3)
C40.091 (4)0.104 (5)0.085 (4)0.076 (4)0.059 (4)0.046 (4)
C50.098 (5)0.106 (5)0.082 (4)0.081 (4)0.058 (4)0.052 (4)
C60.064 (4)0.064 (3)0.086 (4)0.044 (3)0.041 (3)0.034 (3)
C70.073 (4)0.088 (4)0.047 (3)0.055 (3)0.036 (3)0.034 (3)
C80.123 (6)0.162 (7)0.073 (4)0.123 (6)0.062 (4)0.064 (4)
C90.129 (6)0.160 (7)0.065 (4)0.122 (6)0.061 (4)0.070 (4)
C100.050 (3)0.063 (3)0.046 (3)0.035 (3)0.026 (2)0.021 (2)
C110.082 (4)0.093 (4)0.067 (3)0.071 (4)0.050 (3)0.046 (3)
C120.094 (4)0.094 (4)0.064 (3)0.073 (4)0.054 (3)0.050 (3)
C130.23 (2)0.15 (2)0.20 (2)0.062 (19)0.00 (2)0.10 (2)
C140.27 (2)0.124 (12)0.066 (11)0.082 (13)0.017 (13)0.050 (10)
C150.162 (16)0.099 (11)0.17 (2)0.014 (12)0.024 (16)0.035 (12)
C160.229 (17)0.209 (17)0.233 (19)0.099 (14)0.031 (15)0.085 (14)
N170.192 (18)0.28 (3)0.23 (3)0.106 (17)0.02 (2)0.12 (2)
C180.24 (2)0.124 (14)0.120 (17)0.089 (14)0.042 (17)0.043 (12)
Geometric parameters (Å, º) top
I1—Cu12.6891 (9)C9—C101.370 (7)
I1—Cu1i2.8072 (11)C9—H90.9300
Cu1—N11.996 (4)C10—C111.368 (7)
Cu1—N22.000 (4)C11—C121.374 (6)
N1—C11.326 (7)C11—H110.9300
N1—C51.333 (6)C12—H120.9300
N2—C81.311 (7)C13—C13iv1.300 (10)
N2—C121.322 (6)C13—C141.437 (9)
C1—C21.367 (7)C13—H130.9609
C1—H10.9300C14—N17v1.348 (15)
C2—C31.375 (7)C14—C151.363 (9)
C2—H20.9300C14—C181.394 (9)
C3—C41.376 (8)C15—C161.353 (9)
C3—C61.475 (7)C15—N17v1.45 (2)
C4—C51.383 (7)C15—H150.9607
C4—H40.9300C15—Hv1.11 (2)
C5—H50.9300C16—C18v1.348 (9)
C6—C6ii1.314 (10)C16—N171.350 (9)
C6—H60.9300C16—N17v1.362 (9)
C7—C7iii1.297 (9)C16—H160.9608
C7—C101.466 (6)C16—Hv0.967 (18)
C7—H70.9300N17—C18v1.21 (2)
C8—C91.370 (7)N17—N17v1.45 (2)
C8—H80.9300C18—H180.9607
Cu1—I1—Cu1i80.26 (3)N17v—C14—C1564.6 (10)
N1—Cu1—N2127.33 (17)N17v—C14—C1852.3 (10)
N1—Cu1—I1108.03 (13)C15—C14—C18116.2 (10)
N2—Cu1—I1109.45 (12)N17v—C14—C13160.3 (17)
N1—Cu1—I1i107.96 (15)C15—C14—C13126.9 (13)
N2—Cu1—I1i100.67 (13)C18—C14—C13116.2 (11)
I1—Cu1—I1i99.74 (3)C16—C15—C14115.2 (10)
C1—N1—C5115.8 (4)C16—C15—N17v58.1 (6)
C1—N1—Cu1124.3 (3)C14—C15—N17v57.2 (8)
C5—N1—Cu1119.9 (4)C16—C15—H15121.9
C8—N2—C12115.1 (4)C14—C15—H15122.8
C8—N2—Cu1124.8 (3)N17v—C15—H15179.9
C12—N2—Cu1119.5 (3)C16—C15—Hv44.9 (10)
N1—C1—C2124.4 (5)C14—C15—Hv157.2 (16)
N1—C1—H1117.8N17v—C15—Hv102.3 (13)
C2—C1—H1117.8H15—C15—Hv77.6
C1—C2—C3119.9 (5)C18v—C16—N1753.2 (10)
C1—C2—H2120.1C18v—C16—C15172.4 (16)
C3—C2—H2120.1N17—C16—C15129.2 (11)
C2—C3—C4116.6 (4)C18v—C16—N17v116.9 (11)
C2—C3—C6119.8 (5)N17—C16—N17v64.9 (11)
C4—C3—C6123.5 (5)C15—C16—N17v64.5 (9)
C3—C4—C5119.8 (5)C18v—C16—H1662.0
C3—C4—H4120.1N17—C16—H16114.6
C5—C4—H4120.1C15—C16—H16116.1
N1—C5—C4123.5 (5)N17v—C16—H16176.3
N1—C5—H5118.3C18v—C16—Hv125.1 (15)
C4—C5—H5118.3N17—C16—Hv168 (3)
C6ii—C6—C3125.1 (7)C15—C16—Hv54.4 (13)
C6ii—C6—H6117.4N17v—C16—Hv118.0 (18)
C3—C6—H6117.4H16—C16—Hv63.3
C7iii—C7—C10126.7 (6)C18v—N17—C14v65.8 (8)
C7iii—C7—H7116.7C18v—N17—C1663.3 (7)
C10—C7—H7116.7C14v—N17—C16128.9 (12)
N2—C8—C9124.4 (5)C18v—N17—C16v168 (3)
N2—C8—H8117.8C14v—N17—C16v115.6 (11)
C9—C8—H8117.8C16—N17—C16v115.1 (11)
C10—C9—C8120.6 (5)C18v—N17—C15v123.2 (12)
C10—C9—H9119.7C14v—N17—C15v58.2 (7)
C8—C9—H9119.7C16—N17—C15v172.1 (15)
C11—C10—C9115.5 (4)C16v—N17—C15v57.5 (7)
C11—C10—C7123.8 (4)C18v—N17—N17v120.1 (14)
C9—C10—C7120.8 (4)C14v—N17—N17v171 (3)
C10—C11—C12120.1 (5)C16—N17—N17v58.0 (7)
C10—C11—H11120.0C16v—N17—N17v57.1 (7)
C12—C11—H11120.0C15v—N17—N17v114.5 (11)
N2—C12—C11124.4 (5)N17v—C18—C16v63.5 (7)
N2—C12—H12117.8N17v—C18—C1461.9 (9)
C11—C12—H12117.8C16v—C18—C14125.2 (12)
C13iv—C13—C14124.7 (16)N17v—C18—H18176.4
C13iv—C13—H13117.5C16v—C18—H18117.6
C14—C13—H13117.6C14—C18—H18117.2
C5—N1—C1—C21.2 (10)C13iv—C13—C14—C1543 (5)
Cu1—N1—C1—C2178.1 (5)C13iv—C13—C14—C18147 (3)
N1—C1—C2—C31.1 (11)N17v—C14—C15—C162.9 (18)
C1—C2—C3—C42.4 (9)C18—C14—C15—C165.8 (16)
C1—C2—C3—C6178.5 (6)C13—C14—C15—C16164.1 (18)
C2—C3—C4—C51.4 (10)C18—C14—C15—N17v8.7 (18)
C6—C3—C4—C5179.5 (6)C13—C14—C15—N17v161 (2)
C1—N1—C5—C42.3 (10)C14—C15—C16—N171 (2)
Cu1—N1—C5—C4177.0 (5)N17v—C15—C16—N174 (3)
C3—C4—C5—N11.0 (11)C14—C15—C16—N17v2.9 (18)
C2—C3—C6—C6ii172.0 (8)C15—C16—N17—C18v171 (2)
C4—C3—C6—C6ii8.9 (12)N17v—C16—N17—C18v167 (3)
C12—N2—C8—C92.1 (11)C18v—C16—N17—C14v6 (2)
Cu1—N2—C8—C9169.2 (6)C15—C16—N17—C14v177 (2)
N2—C8—C9—C100.4 (13)N17v—C16—N17—C14v173 (5)
C8—C9—C10—C110.9 (11)C18v—C16—N17—C16v167 (3)
C8—C9—C10—C7179.2 (7)C15—C16—N17—C16v4 (3)
C7iii—C7—C10—C111.9 (12)N17v—C16—N17—C16v0.001 (1)
C7iii—C7—C10—C9178.0 (8)C18v—C16—N17—N17v167 (3)
C9—C10—C11—C120.5 (9)C15—C16—N17—N17v4 (3)
C7—C10—C11—C12179.6 (6)C15—C14—C18—N17v10 (2)
C8—N2—C12—C112.6 (10)C13—C14—C18—N17v161 (2)
Cu1—N2—C12—C11169.2 (5)N17v—C14—C18—C16v5 (2)
C10—C11—C12—N21.3 (10)C15—C14—C18—C16v15 (3)
C13iv—C13—C14—N17v163 (4)C13—C14—C18—C16v156 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+2, y+1, z+1; (iii) x, y+2, z+2; (iv) x+2, y+1, z+2; (v) x+1, y+1, z+2.
 

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