Synthesis, crystal structure and Hirshfeld surface analysis of di-μ₂-iodido-bis­[(2,2′-bi­quinoline-κ²N,N′)copper(I)]

In the layer structure of di-μ₂-iodido-bis­[(2,2′-bi­quinoline-κ²N,N′)copper(I)], π–π inter­actions provide conectivity within and between the layers.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.021
• wR factor = 0.050
• Data-to-parameter ratio = 27.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1      .       13.9 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1_a    .       30.5 s.u.
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         17 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.1 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         15 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Di-µ₂-iodido-bis[(2,2'-biquinoline-κ²N,N')copper(I)]

Crystal data

[Cu2I2(C18H12N2)2]	Z = 1
Mr = 893.49	F(000) = 432
Triclinic, P1	Dx = 1.979 Mg m^−3
a = 8.2032 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4084 (3) Å	Cell parameters from 9951 reflections
c = 10.8312 (3) Å	θ = 2.3–32.6°
α = 70.9328 (8)°	µ = 3.51 mm^−1
β = 76.1237 (9)°	T = 100 K
γ = 74.2486 (9)°	Plate, red
V = 749.84 (4) Å^3	0.12 × 0.10 × 0.06 mm

Data collection

Bruker D8 QUEST PHOTON-III CCD diffractometer	4875 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θmax = 32.6°, θmin = 2.3°
Tmin = 0.656, Tmax = 0.798	h = −12→12
22231 measured reflections	k = −14→14
5464 independent reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.0241P)^2 + 0.2045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
5464 reflections	Δρmax = 0.93 e Å^−3
200 parameters	Δρmin = −1.00 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.00061 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.72676 (2)	0.05497 (2)	0.36228 (2)	0.01463 (4)
Cu1	0.47151 (3)	0.14895 (2)	0.52815 (2)	0.01482 (5)
N1	0.50362 (17)	0.22489 (16)	0.68043 (14)	0.0137 (2)
N2	0.32363 (17)	0.37275 (15)	0.48351 (13)	0.0126 (2)
C1	0.5986 (2)	0.14322 (19)	0.77875 (16)	0.0149 (3)
C2	0.7206 (2)	0.0086 (2)	0.76410 (18)	0.0188 (3)
H2	0.7335	−0.0253	0.6881	0.023*
C3	0.8205 (2)	−0.0730 (2)	0.86007 (19)	0.0225 (3)
H3	0.9050	−0.1616	0.8486	0.027*
C4	0.7991 (3)	−0.0268 (2)	0.97589 (19)	0.0235 (4)
H4	0.8658	−0.0869	1.0430	0.028*
C5	0.6831 (2)	0.1034 (2)	0.99178 (18)	0.0221 (3)
H5	0.6688	0.1333	1.0701	0.027*
C6	0.5837 (2)	0.1942 (2)	0.89164 (16)	0.0168 (3)
C7	0.4734 (2)	0.3365 (2)	0.89624 (17)	0.0204 (3)
H7	0.4603	0.3741	0.9702	0.024*
C8	0.3849 (2)	0.4209 (2)	0.79434 (17)	0.0186 (3)
H8	0.3134	0.5187	0.7954	0.022*
C9	0.4017 (2)	0.35984 (18)	0.68682 (16)	0.0134 (3)
C10	0.30656 (19)	0.44564 (18)	0.57445 (16)	0.0130 (3)
C11	0.2064 (2)	0.59515 (18)	0.56565 (17)	0.0151 (3)
H11	0.1989	0.6436	0.6318	0.018*
C12	0.1199 (2)	0.67017 (18)	0.46130 (17)	0.0161 (3)
H12	0.0505	0.7703	0.4552	0.019*
C13	0.1348 (2)	0.59756 (18)	0.36296 (16)	0.0135 (3)
C14	0.0488 (2)	0.6683 (2)	0.25249 (17)	0.0171 (3)
H14	−0.0225	0.7681	0.2431	0.021*
C15	0.0680 (2)	0.5933 (2)	0.15911 (17)	0.0183 (3)
H15	0.0103	0.6413	0.0850	0.022*
C16	0.1738 (2)	0.4440 (2)	0.17292 (17)	0.0181 (3)
H16	0.1868	0.3931	0.1074	0.022*
C17	0.2579 (2)	0.37192 (19)	0.27946 (17)	0.0162 (3)
H17	0.3279	0.2717	0.2876	0.019*
C18	0.23990 (19)	0.44731 (18)	0.37738 (16)	0.0129 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01422 (5)	0.01364 (5)	0.01633 (6)	−0.00129 (3)	−0.00081 (3)	−0.00714 (4)
Cu1	0.01437 (9)	0.01477 (9)	0.01559 (10)	0.00062 (7)	−0.00375 (7)	−0.00671 (7)
N1	0.0120 (6)	0.0154 (6)	0.0140 (6)	−0.0033 (5)	−0.0023 (5)	−0.0041 (5)
N2	0.0117 (5)	0.0134 (6)	0.0131 (6)	−0.0013 (5)	−0.0023 (4)	−0.0049 (5)
C1	0.0130 (7)	0.0179 (7)	0.0145 (7)	−0.0057 (6)	−0.0020 (5)	−0.0035 (6)
C2	0.0187 (8)	0.0184 (7)	0.0188 (8)	−0.0028 (6)	−0.0069 (6)	−0.0028 (6)
C3	0.0211 (8)	0.0196 (8)	0.0249 (9)	−0.0041 (7)	−0.0097 (7)	0.0003 (7)
C4	0.0250 (9)	0.0243 (9)	0.0207 (8)	−0.0102 (7)	−0.0117 (7)	0.0042 (7)
C5	0.0252 (9)	0.0282 (9)	0.0150 (7)	−0.0111 (7)	−0.0076 (6)	−0.0013 (7)
C6	0.0149 (7)	0.0234 (8)	0.0133 (7)	−0.0081 (6)	−0.0018 (5)	−0.0036 (6)
C7	0.0183 (8)	0.0309 (9)	0.0160 (8)	−0.0060 (7)	−0.0015 (6)	−0.0121 (7)
C8	0.0170 (7)	0.0244 (8)	0.0175 (8)	−0.0024 (6)	−0.0030 (6)	−0.0113 (7)
C9	0.0113 (6)	0.0162 (7)	0.0138 (7)	−0.0027 (5)	−0.0015 (5)	−0.0059 (6)
C10	0.0103 (6)	0.0148 (6)	0.0145 (7)	−0.0032 (5)	−0.0009 (5)	−0.0053 (5)
C11	0.0147 (7)	0.0140 (6)	0.0186 (7)	−0.0033 (5)	−0.0016 (5)	−0.0077 (6)
C12	0.0152 (7)	0.0118 (6)	0.0206 (8)	−0.0023 (5)	−0.0009 (6)	−0.0055 (6)
C13	0.0116 (6)	0.0118 (6)	0.0159 (7)	−0.0019 (5)	−0.0022 (5)	−0.0026 (5)
C14	0.0137 (7)	0.0162 (7)	0.0181 (8)	−0.0016 (6)	−0.0033 (6)	−0.0012 (6)
C15	0.0175 (7)	0.0188 (7)	0.0166 (7)	−0.0013 (6)	−0.0058 (6)	−0.0023 (6)
C16	0.0175 (7)	0.0212 (8)	0.0164 (7)	−0.0011 (6)	−0.0043 (6)	−0.0077 (6)
C17	0.0152 (7)	0.0162 (7)	0.0180 (7)	−0.0006 (6)	−0.0036 (6)	−0.0072 (6)
C18	0.0104 (6)	0.0135 (6)	0.0145 (7)	−0.0021 (5)	−0.0016 (5)	−0.0041 (5)

Geometric parameters (Å, º)

I1—Cu1	2.5734 (2)	C7—C8	1.369 (3)
I1—Cu1^i	2.6487 (2)	C7—H7	0.9500
Cu1—N2	2.0900 (14)	C8—C9	1.422 (2)
Cu1—N1	2.0930 (13)	C8—H8	0.9500
Cu1—I1^i	2.6487 (2)	C9—C10	1.488 (2)
Cu1—Cu1^i	2.9520 (4)	C10—C11	1.409 (2)
N1—C9	1.330 (2)	C11—C12	1.367 (2)
N1—C1	1.367 (2)	C11—H11	0.9500
N2—C10	1.3354 (19)	C12—C13	1.409 (2)
N2—C18	1.369 (2)	C12—H12	0.9500
C1—C2	1.414 (2)	C13—C14	1.415 (2)
C1—C6	1.421 (2)	C13—C18	1.423 (2)
C2—C3	1.374 (2)	C14—C15	1.369 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.415 (3)	C15—C16	1.418 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.365 (3)	C16—C17	1.372 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.418 (2)	C17—C18	1.418 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.406 (3)
Cu1—I1—Cu1^i	68.829 (8)	C8—C7—H7	119.9
N2—Cu1—N1	79.28 (5)	C6—C7—H7	119.9
N2—Cu1—I1	122.14 (4)	C7—C8—C9	118.99 (16)
N1—Cu1—I1	122.34 (4)	C7—C8—H8	120.5
N2—Cu1—I1^i	110.91 (4)	C9—C8—H8	120.5
N1—Cu1—I1^i	106.99 (4)	N1—C9—C8	122.17 (15)
I1—Cu1—I1^i	111.171 (8)	N1—C9—C10	116.58 (13)
N2—Cu1—Cu1^i	141.62 (4)	C8—C9—C10	121.24 (15)
N1—Cu1—Cu1^i	136.76 (4)	N2—C10—C11	122.82 (15)
I1—Cu1—Cu1^i	56.791 (7)	N2—C10—C9	115.92 (14)
I1^i—Cu1—Cu1^i	54.380 (7)	C11—C10—C9	121.26 (14)
C9—N1—C1	119.18 (14)	C12—C11—C10	119.63 (14)
C9—N1—Cu1	113.35 (11)	C12—C11—H11	120.2
C1—N1—Cu1	126.92 (11)	C10—C11—H11	120.2
C10—N2—C18	118.23 (14)	C11—C12—C13	119.38 (15)
C10—N2—Cu1	113.89 (11)	C11—C12—H12	120.3
C18—N2—Cu1	127.82 (10)	C13—C12—H12	120.3
N1—C1—C2	118.85 (15)	C12—C13—C14	122.40 (15)
N1—C1—C6	121.75 (15)	C12—C13—C18	117.93 (15)
C2—C1—C6	119.33 (16)	C14—C13—C18	119.67 (14)
C3—C2—C1	119.82 (17)	C15—C14—C13	120.22 (16)
C3—C2—H2	120.1	C15—C14—H14	119.9
C1—C2—H2	120.1	C13—C14—H14	119.9
C2—C3—C4	120.78 (18)	C14—C15—C16	120.11 (16)
C2—C3—H3	119.6	C14—C15—H15	119.9
C4—C3—H3	119.6	C16—C15—H15	119.9
C5—C4—C3	120.43 (17)	C17—C16—C15	121.04 (15)
C5—C4—H4	119.8	C17—C16—H16	119.5
C3—C4—H4	119.8	C15—C16—H16	119.5
C4—C5—C6	120.13 (17)	C16—C17—C18	119.85 (15)
C4—C5—H5	119.9	C16—C17—H17	120.1
C6—C5—H5	119.9	C18—C17—H17	120.1
C7—C6—C5	122.99 (16)	N2—C18—C17	118.90 (14)
C7—C6—C1	117.63 (16)	N2—C18—C13	122.00 (14)
C5—C6—C1	119.34 (17)	C17—C18—C13	119.10 (15)
C8—C7—C6	120.15 (15)
C9—N1—C1—C2	−173.05 (15)	C18—N2—C10—C9	−179.42 (13)
Cu1—N1—C1—C2	16.1 (2)	Cu1—N2—C10—C9	3.07 (17)
C9—N1—C1—C6	3.8 (2)	N1—C9—C10—N2	4.8 (2)
Cu1—N1—C1—C6	−166.98 (11)	C8—C9—C10—N2	−175.83 (14)
N1—C1—C2—C3	178.35 (16)	N1—C9—C10—C11	−174.64 (14)
C6—C1—C2—C3	1.4 (3)	C8—C9—C10—C11	4.7 (2)
C1—C2—C3—C4	2.0 (3)	N2—C10—C11—C12	0.9 (2)
C2—C3—C4—C5	−2.6 (3)	C9—C10—C11—C12	−179.63 (15)
C3—C4—C5—C6	−0.4 (3)	C10—C11—C12—C13	−1.0 (2)
C4—C5—C6—C7	−174.13 (17)	C11—C12—C13—C14	179.90 (16)
C4—C5—C6—C1	3.8 (3)	C11—C12—C13—C18	0.2 (2)
N1—C1—C6—C7	−3.1 (2)	C12—C13—C14—C15	179.67 (15)
C2—C1—C6—C7	173.76 (16)	C18—C13—C14—C15	−0.7 (2)
N1—C1—C6—C5	178.82 (15)	C13—C14—C15—C16	0.2 (3)
C2—C1—C6—C5	−4.3 (2)	C14—C15—C16—C17	0.3 (3)
C5—C6—C7—C8	177.99 (17)	C15—C16—C17—C18	−0.3 (3)
C1—C6—C7—C8	0.0 (2)	C10—N2—C18—C17	179.51 (14)
C6—C7—C8—C9	2.2 (3)	Cu1—N2—C18—C17	−3.4 (2)
C1—N1—C9—C8	−1.5 (2)	C10—N2—C18—C13	−0.9 (2)
Cu1—N1—C9—C8	170.55 (12)	Cu1—N2—C18—C13	176.23 (11)
C1—N1—C9—C10	177.85 (13)	C16—C17—C18—N2	179.42 (15)
Cu1—N1—C9—C10	−10.14 (17)	C16—C17—C18—C13	−0.2 (2)
C7—C8—C9—N1	−1.6 (3)	C12—C13—C18—N2	0.7 (2)
C7—C8—C9—C10	179.14 (15)	C14—C13—C18—N2	−178.92 (15)
C18—N2—C10—C11	0.1 (2)	C12—C13—C18—C17	−179.65 (15)
Cu1—N2—C10—C11	−177.45 (12)	C14—C13—C18—C17	0.7 (2)

Symmetry code: (i) −x+1, −y, −z+1.