Structural diversity in copper(I) iodide complexes with 6-thioxopiperidin-2-one, piperidine-2,6-di­thione and isoindoline-1,3-di­thione ligands

Wheaton, A.M.; Guzei, I.A.; Berry, J.F.

doi:10.1107/S2056989020009676

Structural diversity in copper(I) iodide complexes with 6-thioxopiperidin-2-one, piperidine-2,6-dithione and isoindoline-1,3-dithione ligands

A. M. Wheaton, I. A. Guzei and J. F. Berry

Five copper(I) iodide coordination compounds were synthesized and characterized by single-crystal X-ray diffraction measurements; the resulting structures display a diverse array of structural features.

Keywords: crystal structure; copper(I) iodide; coordination complexes.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020009676/zl2791sup1.cif Contains datablocks I, II, III, IV, V
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020009676/zl2791Isup7.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020009676/zl2791IIsup8.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020009676/zl2791IIIsup9.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020009676/zl2791IVsup10.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020009676/zl2791Vsup11.hkl Contains datablock V

CCDC references: 2016675; 2016674; 2016673; 2016672; 2016671

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Mean (C-C) = 0.005 Å
Mean (C-C) = 0.007 Å
Mean (C-C) = 0.008 Å
Mean (C-C) = 0.011 Å
R factor = 0.012
wR factor = 0.030
Data-to-parameter ratio = 33.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 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          2 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C6       --C7       .        7.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1      .       25.3 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1_a    .       54.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1      --S1       .        8.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cu1      --N2       .        7.8 s.u.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        281 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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




Datablock: II


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Author Response: These reflections were excluded during the data integration.

PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Author Response: This is an informational alert.


Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       8.12 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1      .       13.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu2      .       27.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu2_a    .       21.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I2       --Cu1      .       16.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I2       --Cu2      .       18.3 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I2       --Cu1_a    .       23.0 s.u.
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.22 Ratio
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         28 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: III



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.26 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          2 Note
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1      .        7.8 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1_a    .        8.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1_d    .        9.5 s.u.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         10 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: IV


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.26 Report

Author Response: Author Response: The large ratio between the maximum and minimum peaks of residual electron density is due to the presence of several peaks (ca. 1.6 e-/ \%A^3^) of electron density in the final structural model. These peaks were in the vicinity of atoms I1 and I2, and were considered noise.

PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT014_ALERT_1_G N.O.K.   _shelx_fab_checksum Found in CIF ......     Please Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1_a    .        9.8 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I2       --Cu2      .        6.5 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I2       --Cu2_c    .        8.8 s.u.
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure        195 A   3  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         22 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: V


Alert level B
PLAT971_ALERT_2_B Check Calcd Resid. Dens.  0.71A   From I1              3.04 eA-3

Author Response: The final difference Fourier map contained several peaks of residual electron density (c.a. 3.0 - 1.5 e^-^/\%A^3^), located in the vicinity of atom I1. These peaks were in chemically unreasonable positions and were considered noise.


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.81 Report

Author Response: The large ratio of maximum/minimum residual is due to the presence of several peaks of residual electron density (c.a. 3.0 - 1.5 e^-^/\%A^3^), located in the vicinity of atom I1. T hese peaks were in chemically unreasonable positions and were considered noise.

PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.011 Ang.

Author Response: This was the best achievable precision with the given data.

PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.01A   From I1              1.56 eA-3

PLAT971_ALERT_2_C Check Calcd Resid. Dens.  1.56A   From Cu1             1.54 eA-3

PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       7.02 Why ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1      .        7.4 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1       --Cu1_a    .        7.4 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         51 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2017) for (I), (V); APEX2 (Bruker, 2013) for (II), (III), (IV). Cell refinement: APEX3 (Bruker, 2017) for (I), (V); SAINT (Bruker, 2013) for (II), (III), (IV). Data reduction: APEX3 (Bruker, 2017) for (I), (V); SAINT (Bruker, 2013) for (II), (III), (IV). For all structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Di-µ-iodido-bis[(acetonitrile-κN)(6-sulfanylidenepiperidin-2-one-κS)copper(I)] (I) top

Crystal data top

[Cu₂I₂(C₂H₃N)₂(C₅H₇NOS)₂]	Z = 1
M_r = 721.34	F(000) = 344
Triclinic, P1	D_x = 2.165 Mg m⁻³
a = 8.121 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.433 (2) Å	Cell parameters from 9905 reflections
c = 9.154 (2) Å	θ = 2.4–33.6°
α = 68.918 (12)°	µ = 4.92 mm⁻¹
β = 80.523 (12)°	T = 100 K
γ = 71.270 (9)°	Block, yellow
V = 553.2 (2) Å³	0.15 × 0.13 × 0.13 mm

Data collection top

Bruker APEXII Quazar diffractometer	4099 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	3988 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.021
Detector resolution: 7.9 pixels mm^-1	θ_max = 33.6°, θ_min = 2.4°
0.5° ω and 0.5° φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −12→13
T_min = 0.079, T_max = 0.120	l = −14→13
17922 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.012	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.030	w = 1/[σ²(F_o²) + (0.010P)² + 0.2P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4099 reflections	Δρ_max = 0.43 e Å⁻³
122 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.71563 (2)	0.27834 (2)	−0.05209 (2)	0.01894 (2)
Cu1	0.45123 (2)	0.38128 (2)	0.13294 (2)	0.01894 (3)
S1	0.56399 (3)	0.24010 (4)	0.37914 (3)	0.01986 (5)
O1	0.05297 (11)	0.66482 (10)	0.51701 (10)	0.02183 (14)
N1	0.28752 (11)	0.45357 (12)	0.47278 (10)	0.01722 (15)
H1	0.278 (2)	0.5149 (19)	0.3753 (15)	0.021*
N2	0.26648 (13)	0.25871 (13)	0.15713 (11)	0.02214 (17)
C1	0.41889 (13)	0.30218 (13)	0.51318 (11)	0.01629 (16)
C2	0.42947 (14)	0.19443 (14)	0.68381 (12)	0.02105 (18)
H2A	0.508966	0.227581	0.731337	0.025*
H2B	0.479000	0.067327	0.694709	0.025*
C3	0.25216 (15)	0.22197 (14)	0.77191 (12)	0.02196 (19)
H3A	0.265859	0.157362	0.885379	0.026*
H3B	0.176642	0.174405	0.734521	0.026*
C4	0.16790 (15)	0.41932 (14)	0.74515 (12)	0.02137 (19)
H4A	0.048628	0.437280	0.795116	0.026*
H4B	0.235816	0.462532	0.795254	0.026*
C5	0.15956 (13)	0.52448 (13)	0.57383 (12)	0.01738 (17)
C6	0.17193 (13)	0.17425 (13)	0.20890 (12)	0.01823 (17)
C7	0.05487 (15)	0.06411 (15)	0.27580 (14)	0.02279 (19)
H7A	0.012545	0.043830	0.191652	0.034*
H7B	−0.044124	0.123970	0.332437	0.034*
H7C	0.117167	−0.049821	0.348452	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02097 (3)	0.01735 (3)	0.01597 (3)	−0.00396 (2)	0.00281 (2)	−0.00554 (2)
Cu1	0.02026 (6)	0.01995 (6)	0.01757 (6)	−0.00817 (5)	0.00300 (4)	−0.00688 (5)
S1	0.01667 (10)	0.02251 (11)	0.01925 (11)	−0.00292 (9)	0.00063 (8)	−0.00856 (9)
O1	0.0229 (4)	0.0176 (3)	0.0234 (4)	−0.0036 (3)	0.0001 (3)	−0.0073 (3)
N1	0.0191 (4)	0.0168 (4)	0.0141 (3)	−0.0045 (3)	0.0007 (3)	−0.0044 (3)
N2	0.0219 (4)	0.0223 (4)	0.0229 (4)	−0.0073 (3)	0.0004 (3)	−0.0079 (3)
C1	0.0164 (4)	0.0175 (4)	0.0165 (4)	−0.0059 (3)	−0.0013 (3)	−0.0062 (3)
C2	0.0237 (5)	0.0204 (4)	0.0161 (4)	−0.0028 (4)	−0.0038 (3)	−0.0044 (3)
C3	0.0292 (5)	0.0181 (4)	0.0165 (4)	−0.0082 (4)	0.0017 (4)	−0.0033 (3)
C4	0.0270 (5)	0.0200 (4)	0.0159 (4)	−0.0075 (4)	0.0037 (4)	−0.0059 (3)
C5	0.0192 (4)	0.0169 (4)	0.0176 (4)	−0.0071 (3)	0.0020 (3)	−0.0071 (3)
C6	0.0180 (4)	0.0177 (4)	0.0183 (4)	−0.0029 (3)	−0.0013 (3)	−0.0069 (3)
C7	0.0233 (5)	0.0219 (5)	0.0254 (5)	−0.0108 (4)	0.0042 (4)	−0.0088 (4)

Geometric parameters (Å, º) top

I1—Cu1	2.6261 (6)	C2—H2B	0.9900
I1—Cu1ⁱ	2.6321 (7)	C2—C3	1.5216 (16)
Cu1—Cu1ⁱ	2.7274 (6)	C3—H3A	0.9900
Cu1—S1	2.3205 (6)	C3—H3B	0.9900
Cu1—N2	2.0225 (10)	C3—C4	1.5260 (16)
S1—C1	1.6607 (11)	C4—H4A	0.9900
O1—C5	1.2117 (13)	C4—H4B	0.9900
N1—H1	0.857 (12)	C4—C5	1.4988 (15)
N1—C1	1.3493 (13)	C6—C7	1.4518 (15)
N1—C5	1.4055 (13)	C7—H7A	0.9800
N2—C6	1.1446 (14)	C7—H7B	0.9800
C1—C2	1.4987 (15)	C7—H7C	0.9800
C2—H2A	0.9900

Cu1—I1—Cu1ⁱ	62.489 (13)	C3—C2—H2B	109.2
I1—Cu1—I1ⁱ	117.511 (13)	C2—C3—H3A	109.7
I1ⁱ—Cu1—Cu1ⁱ	58.647 (16)	C2—C3—H3B	109.7
I1—Cu1—Cu1ⁱ	58.864 (17)	C2—C3—C4	109.71 (9)
S1—Cu1—I1	102.61 (2)	H3A—C3—H3B	108.2
S1—Cu1—I1ⁱ	118.719 (16)	C4—C3—H3A	109.7
S1—Cu1—Cu1ⁱ	132.375 (17)	C4—C3—H3B	109.7
N2—Cu1—I1ⁱ	105.18 (3)	C3—C4—H4A	109.3
N2—Cu1—I1	111.38 (3)	C3—C4—H4B	109.3
N2—Cu1—Cu1ⁱ	127.14 (3)	H4A—C4—H4B	108.0
N2—Cu1—S1	100.19 (3)	C5—C4—C3	111.49 (9)
C1—S1—Cu1	109.94 (4)	C5—C4—H4A	109.3
C1—N1—H1	118.1 (10)	C5—C4—H4B	109.3
C1—N1—C5	127.15 (9)	O1—C5—N1	118.17 (9)
C5—N1—H1	114.7 (10)	O1—C5—C4	125.23 (10)
C6—N2—Cu1	162.96 (9)	N1—C5—C4	116.60 (9)
N1—C1—S1	121.16 (8)	N2—C6—C7	178.87 (12)
N1—C1—C2	117.20 (9)	C6—C7—H7A	109.5
C2—C1—S1	121.63 (8)	C6—C7—H7B	109.5
C1—C2—H2A	109.2	C6—C7—H7C	109.5
C1—C2—H2B	109.2	H7A—C7—H7B	109.5
C1—C2—C3	112.14 (9)	H7A—C7—H7C	109.5
H2A—C2—H2B	107.9	H7B—C7—H7C	109.5
C3—C2—H2A	109.2

Cu1—S1—C1—N1	−20.58 (9)	C1—C2—C3—C4	−54.31 (12)
Cu1—S1—C1—C2	160.32 (7)	C2—C3—C4—C5	54.18 (12)
S1—C1—C2—C3	−153.63 (8)	C3—C4—C5—O1	153.16 (10)
N1—C1—C2—C3	27.24 (13)	C3—C4—C5—N1	−27.45 (13)
C1—N1—C5—O1	178.41 (10)	C5—N1—C1—S1	−177.90 (8)
C1—N1—C5—C4	−1.02 (15)	C5—N1—C1—C2	1.24 (15)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1ⁱ	0.86 (1)	2.85 (1)	3.6980 (12)	174 (1)

Symmetry code: (i) −x+1, −y+1, −z.

Bis(acetonitrile-κN)tetra-µ₃-iodido-bis(6-sulfanylidenepiperidin-2-one-κS)-tetrahedro-tetracopper(I) (II) top

Crystal data top

[Cu₄I₄(C₂H₃N)₂(C₅H₇NOS)₂]	F(000) = 2032
M_r = 1102.22	D_x = 2.639 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 14.4669 (8) Å	Cell parameters from 9916 reflections
b = 12.2157 (7) Å	θ = 4.9–73.4°
c = 16.9969 (11) Å	µ = 39.97 mm⁻¹
β = 112.562 (5)°	T = 105 K
V = 2773.9 (3) Å³	Block, yellow
Z = 4	0.1 × 0.08 × 0.04 mm

Data collection top

Bruker SMART APEXII area detector diffractometer	2753 independent reflections
Radiation source: sealed X-ray tube, Siemens, K FFCU 2K 90	2669 reflections with I > 2σ(I)
Equatorially mounted graphite monochromator	R_int = 0.060
Detector resolution: 7.9 pixels mm^-1	θ_max = 73.4°, θ_min = 4.9°
0.60° ω and 0.6° φ scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −15→15
T_min = 0.042, T_max = 0.188	l = −19→20
23553 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0336P)² + 8.1228P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2753 reflections	Δρ_max = 0.84 e Å⁻³
140 parameters	Δρ_min = −1.25 e Å⁻³
1 restraint

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.60668 (2)	0.86418 (2)	0.17606 (2)	0.01452 (8)
I2	0.64470 (2)	0.62302 (2)	0.36802 (2)	0.01064 (8)
Cu1	0.56033 (4)	0.66150 (4)	0.20182 (3)	0.01367 (13)
Cu2	0.57587 (4)	0.82337 (4)	0.32174 (3)	0.01552 (13)
S1	0.60446 (7)	0.54868 (7)	0.11461 (5)	0.01569 (19)
O1	0.6145 (2)	0.2772 (2)	0.32682 (16)	0.0174 (6)
N1	0.6055 (2)	0.3917 (3)	0.22074 (19)	0.0126 (6)
H1	0.606 (4)	0.445 (3)	0.255 (2)	0.015*
N2	0.6525 (3)	0.9386 (3)	0.4015 (2)	0.0169 (7)
C1	0.6091 (3)	0.4194 (3)	0.1448 (2)	0.0123 (7)
C2	0.6188 (3)	0.3267 (3)	0.0903 (2)	0.0159 (8)
H2A	0.690589	0.314522	0.102177	0.019*
H2B	0.585384	0.347436	0.029590	0.019*
C3	0.5734 (3)	0.2208 (3)	0.1056 (2)	0.0202 (8)
H3A	0.587416	0.160825	0.072514	0.024*
H3B	0.499919	0.228893	0.086154	0.024*
C4	0.6177 (3)	0.1928 (3)	0.2001 (3)	0.0191 (8)
H4A	0.581117	0.129536	0.210478	0.023*
H4B	0.688502	0.170761	0.216276	0.023*
C5	0.6128 (3)	0.2859 (3)	0.2552 (2)	0.0132 (7)
C6	0.6848 (3)	1.0148 (3)	0.4409 (2)	0.0148 (7)
C7	0.7242 (3)	1.1137 (3)	0.4894 (2)	0.0180 (8)
H7A	0.709649	1.176523	0.450663	0.027*
H7B	0.796763	1.106656	0.519796	0.027*
H7C	0.692732	1.124854	0.530632	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01753 (14)	0.01161 (13)	0.01566 (13)	−0.00092 (8)	0.00776 (10)	0.00418 (7)
I2	0.01430 (13)	0.01007 (13)	0.00576 (12)	0.00111 (7)	0.00185 (9)	0.00183 (7)
Cu1	0.0197 (3)	0.0114 (3)	0.0103 (2)	0.0035 (2)	0.0062 (2)	0.00158 (19)
Cu2	0.0167 (3)	0.0119 (3)	0.0134 (2)	−0.0027 (2)	0.0007 (2)	−0.00354 (19)
S1	0.0246 (5)	0.0150 (4)	0.0113 (4)	0.0070 (3)	0.0112 (4)	0.0050 (3)
O1	0.0214 (14)	0.0183 (13)	0.0118 (11)	−0.0011 (11)	0.0056 (11)	0.0035 (10)
N1	0.0198 (17)	0.0107 (14)	0.0071 (13)	0.0003 (12)	0.0049 (12)	−0.0007 (11)
N2	0.0173 (16)	0.0157 (16)	0.0139 (14)	−0.0037 (13)	0.0019 (12)	−0.0027 (13)
C1	0.0123 (17)	0.0152 (18)	0.0078 (14)	0.0021 (13)	0.0021 (13)	0.0000 (13)
C2	0.0216 (19)	0.0150 (18)	0.0118 (15)	0.0062 (15)	0.0071 (15)	−0.0020 (13)
C3	0.023 (2)	0.019 (2)	0.0190 (18)	−0.0007 (16)	0.0083 (16)	−0.0087 (15)
C4	0.027 (2)	0.0127 (18)	0.0225 (18)	−0.0004 (15)	0.0145 (17)	−0.0027 (15)
C5	0.0111 (17)	0.0135 (17)	0.0132 (16)	−0.0019 (13)	0.0029 (14)	−0.0001 (13)
C6	0.0169 (18)	0.0143 (18)	0.0091 (14)	0.0025 (14)	0.0003 (14)	0.0011 (14)
C7	0.029 (2)	0.0071 (17)	0.0103 (16)	−0.0010 (15)	−0.0003 (15)	−0.0020 (13)

Geometric parameters (Å, º) top

I1—Cu1	2.6451 (6)	N1—C5	1.405 (5)
I1—Cu2ⁱ	2.7017 (7)	N2—C6	1.137 (5)
I1—Cu2	2.7250 (6)	C1—C2	1.504 (5)
I2—Cu1	2.6542 (6)	C2—H2A	0.9900
I2—Cu1ⁱ	2.7796 (6)	C2—H2B	0.9900
I2—Cu2	2.6456 (6)	C2—C3	1.518 (6)
Cu1—Cu1ⁱ	2.8150 (11)	C3—H3A	0.9900
Cu1—Cu2	2.7864 (8)	C3—H3B	0.9900
Cu1—Cu2ⁱ	2.7106 (8)	C3—C4	1.523 (5)
Cu2—Cu2ⁱ	2.5803 (10)	C4—H4A	0.9900
Cu1—S1	2.2869 (10)	C4—H4B	0.9900
Cu2—N2	1.974 (3)	C4—C5	1.492 (5)
S1—C1	1.654 (4)	C6—C7	1.451 (5)
O1—C5	1.213 (5)	C7—H7A	0.9800
N1—H1	0.870 (19)	C7—H7B	0.9800
N1—C1	1.354 (5)	C7—H7C	0.9800

Cu1—I1—Cu2ⁱ	60.911 (18)	N2—Cu2—I1ⁱ	98.80 (11)
Cu1—I1—Cu2	62.493 (17)	N2—Cu2—I1	104.44 (10)
Cu2ⁱ—I1—Cu2	56.78 (2)	N2—Cu2—I2	114.05 (10)
Cu1—I2—Cu1ⁱ	62.35 (2)	N2—Cu2—Cu1	151.07 (11)
Cu2—I2—Cu1	63.439 (17)	N2—Cu2—Cu1ⁱ	143.75 (11)
Cu2—I2—Cu1ⁱ	59.892 (17)	N2—Cu2—Cu2ⁱ	134.36 (10)
I1—Cu1—I2	107.43 (2)	C1—S1—Cu1	111.24 (13)
I1—Cu1—I2ⁱ	112.60 (2)	C1—N1—H1	117 (3)
I1—Cu1—Cu1ⁱ	110.454 (13)	C1—N1—C5	127.1 (3)
I1—Cu1—Cu2ⁱ	60.576 (18)	C5—N1—H1	115 (3)
I1—Cu1—Cu2	60.157 (18)	C6—N2—Cu2	169.7 (3)
I2—Cu1—I2ⁱ	113.84 (2)	N1—C1—S1	121.6 (3)
I2—Cu1—Cu1ⁱ	61.007 (19)	N1—C1—C2	116.4 (3)
I2ⁱ—Cu1—Cu1ⁱ	56.64 (2)	C2—C1—S1	122.0 (3)
I2ⁱ—Cu1—Cu2	101.87 (2)	C1—C2—H2A	109.0
I2—Cu1—Cu2ⁱ	107.32 (2)	C1—C2—H2B	109.0
I2—Cu1—Cu2	58.129 (16)	C1—C2—C3	112.8 (3)
Cu2ⁱ—Cu1—I2ⁱ	57.602 (18)	H2A—C2—H2B	107.8
Cu2ⁱ—Cu1—Cu1ⁱ	60.53 (2)	C3—C2—H2A	109.0
Cu2—Cu1—Cu1ⁱ	57.881 (18)	C3—C2—H2B	109.0
Cu2ⁱ—Cu1—Cu2	55.97 (2)	C2—C3—H3A	109.7
S1—Cu1—I1	107.77 (3)	C2—C3—H3B	109.7
S1—Cu1—I2ⁱ	97.98 (3)	C2—C3—C4	109.7 (3)
S1—Cu1—I2	117.03 (3)	H3A—C3—H3B	108.2
S1—Cu1—Cu1ⁱ	140.07 (3)	C4—C3—H3A	109.7
S1—Cu1—Cu2	159.65 (4)	C4—C3—H3B	109.7
S1—Cu1—Cu2ⁱ	135.38 (3)	C3—C4—H4A	109.0
I1ⁱ—Cu2—I1	118.71 (2)	C3—C4—H4B	109.0
I1ⁱ—Cu2—Cu1ⁱ	58.512 (18)	H4A—C4—H4B	107.8
I1ⁱ—Cu2—Cu1	109.64 (2)	C5—C4—C3	112.9 (3)
I1—Cu2—Cu1	57.350 (16)	C5—C4—H4A	109.0
I2—Cu2—I1ⁱ	115.15 (2)	C5—C4—H4B	109.0
I2—Cu2—I1	105.38 (2)	O1—C5—N1	117.9 (3)
I2—Cu2—Cu1ⁱ	62.509 (18)	O1—C5—C4	125.1 (3)
I2—Cu2—Cu1	58.432 (17)	N1—C5—C4	117.0 (3)
Cu1ⁱ—Cu2—I1	111.24 (2)	N2—C6—C7	178.5 (4)
Cu1ⁱ—Cu2—Cu1	61.59 (3)	C6—C7—H7A	109.5
Cu2ⁱ—Cu2—I1	61.16 (2)	C6—C7—H7B	109.5
Cu2ⁱ—Cu2—I1ⁱ	62.06 (2)	C6—C7—H7C	109.5
Cu2ⁱ—Cu2—I2	111.572 (12)	H7A—C7—H7B	109.5
Cu2ⁱ—Cu2—Cu1	60.528 (19)	H7A—C7—H7C	109.5
Cu2ⁱ—Cu2—Cu1ⁱ	63.50 (2)	H7B—C7—H7C	109.5

Cu1—S1—C1—N1	−11.4 (4)	C1—C2—C3—C4	−53.9 (4)
Cu1—S1—C1—C2	169.3 (3)	C2—C3—C4—C5	51.0 (5)
S1—C1—C2—C3	−152.4 (3)	C3—C4—C5—O1	156.9 (4)
N1—C1—C2—C3	28.3 (5)	C3—C4—C5—N1	−22.9 (5)
C1—N1—C5—O1	175.3 (4)	C5—N1—C1—S1	−177.2 (3)
C1—N1—C5—C4	−4.9 (6)	C5—N1—C1—C2	2.1 (6)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I2	0.87 (2)	2.81 (2)	3.672 (3)	170 (4)

catena-Poly[[(µ-6-sulfanylidenepiperidin-2-one-κ²O:S)copper(I)]-µ₃-iodido] (III) top

Crystal data top

[CuI(C₅H₇NOS)]	D_x = 2.612 Mg m⁻³
M_r = 319.62	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbcn	Cell parameters from 6676 reflections
a = 26.982 (11) Å	θ = 3.3–73.1°
b = 8.195 (4) Å	µ = 35.47 mm⁻¹
c = 7.351 (3) Å	T = 100 K
V = 1625.4 (13) Å³	Plate, orange
Z = 8	0.08 × 0.07 × 0.03 mm
F(000) = 1200

Data collection top

Bruker SMART APEXII area detector diffractometer	1631 independent reflections
Radiation source: sealed X-ray tube, Siemens, K FFCU 2K 90	1467 reflections with I > 2σ(I)
Equatorially mounted graphite monochromator	R_int = 0.051
Detector resolution: 7.9 pixels mm^-1	θ_max = 73.6°, θ_min = 3.3°
0.60° ω and 0.6° φ scans	h = −32→33
Absorption correction: multi-scan SADABS; Bruker, 2016)	k = −10→9
T_min = 0.030, T_max = 0.144	l = −9→9
25274 measured reflections

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.055P)² + 1.1889P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1631 reflections	Δρ_max = 1.31 e Å⁻³
94 parameters	Δρ_min = −1.03 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.23415 (2)	0.59898 (3)	0.50901 (3)	0.02390 (13)
Cu1	0.28100 (2)	0.62683 (8)	0.82066 (9)	0.02635 (18)
S1	0.36555 (4)	0.63113 (12)	0.83026 (14)	0.0266 (2)
O1	0.50567 (13)	0.2890 (4)	0.9865 (4)	0.0346 (8)
N1	0.43783 (13)	0.4297 (5)	0.9030 (5)	0.0274 (8)
H1	0.4550 (18)	0.516 (4)	0.923 (7)	0.033*
C1	0.38916 (15)	0.4443 (5)	0.8540 (6)	0.0253 (8)
C2	0.35970 (15)	0.2932 (5)	0.8285 (6)	0.0269 (8)
H2A	0.334849	0.311483	0.731519	0.032*
H2B	0.341637	0.268491	0.942412	0.032*
C3	0.39185 (16)	0.1470 (5)	0.7775 (7)	0.0303 (9)
H3A	0.405740	0.162739	0.654072	0.036*
H3B	0.371432	0.046611	0.776524	0.036*
C4	0.43403 (17)	0.1289 (6)	0.9153 (7)	0.0333 (10)
H4A	0.420142	0.095872	1.034455	0.040*
H4B	0.456863	0.041794	0.874268	0.040*
C5	0.46238 (17)	0.2851 (6)	0.9374 (6)	0.0299 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02516 (19)	0.0217 (2)	0.02479 (19)	0.00135 (8)	0.00003 (9)	−0.00010 (9)
Cu1	0.0258 (3)	0.0243 (3)	0.0290 (4)	0.0002 (2)	−0.0002 (2)	0.0001 (3)
S1	0.0245 (5)	0.0238 (5)	0.0315 (5)	0.0009 (4)	−0.0001 (4)	−0.0002 (4)
O1	0.0273 (16)	0.0285 (16)	0.048 (2)	0.0009 (14)	−0.0039 (13)	−0.0007 (14)
N1	0.0253 (18)	0.0211 (17)	0.036 (2)	−0.0028 (13)	0.0010 (15)	−0.0012 (15)
C1	0.0257 (19)	0.025 (2)	0.0252 (19)	0.0017 (16)	0.0007 (16)	−0.0006 (17)
C2	0.0245 (19)	0.025 (2)	0.031 (2)	−0.0007 (16)	0.0000 (17)	−0.0015 (17)
C3	0.029 (2)	0.023 (2)	0.039 (2)	−0.0018 (16)	0.0003 (18)	−0.0042 (19)
C4	0.029 (2)	0.025 (2)	0.046 (3)	−0.0004 (18)	−0.001 (2)	0.001 (2)
C5	0.028 (2)	0.028 (2)	0.034 (2)	0.0032 (17)	0.0023 (17)	0.0001 (19)

Geometric parameters (Å, º) top

I1—Cu1	2.6264 (11)	C2—H2A	0.9900
I1—Cu1ⁱ	2.6709 (12)	C2—H2B	0.9900
I1—Cu1ⁱⁱ	2.6342 (10)	C2—C3	1.526 (6)
Cu1—S1	2.2827 (15)	C3—H3A	0.9900
S1—C1	1.668 (4)	C3—H3B	0.9900
O1—C5	1.223 (6)	C3—C4	1.531 (6)
N1—H1	0.86 (2)	C4—H4A	0.9900
N1—C1	1.367 (6)	C4—H4B	0.9900
N1—C5	1.381 (6)	C4—C5	1.500 (6)
C1—C2	1.483 (6)

Cu1—I1—Cu1ⁱⁱ	106.77 (3)	H2A—C2—H2B	107.8
Cu1—I1—Cu1ⁱ	116.92 (2)	C3—C2—H2A	109.1
Cu1ⁱⁱ—I1—Cu1ⁱ	113.08 (4)	C3—C2—H2B	109.1
I1ⁱⁱⁱ—Cu1—I1^iv	104.19 (4)	C2—C3—H3A	109.7
I1—Cu1—I1^iv	116.85 (3)	C2—C3—H3B	109.7
I1—Cu1—I1ⁱⁱⁱ	99.58 (3)	C2—C3—C4	109.6 (4)
S1—Cu1—I1^iv	97.12 (4)	H3A—C3—H3B	108.2
S1—Cu1—I1	120.62 (4)	C4—C3—H3A	109.7
S1—Cu1—I1ⁱⁱⁱ	118.31 (4)	C4—C3—H3B	109.7
C1—S1—Cu1	111.76 (15)	C3—C4—H4A	109.3
C1—N1—H1	120 (4)	C3—C4—H4B	109.3
C1—N1—C5	125.7 (4)	H4A—C4—H4B	108.0
C5—N1—H1	115 (4)	C5—C4—C3	111.6 (4)
N1—C1—S1	118.4 (3)	C5—C4—H4A	109.3
N1—C1—C2	118.3 (4)	C5—C4—H4B	109.3
C2—C1—S1	123.3 (3)	O1—C5—N1	119.3 (4)
C1—C2—H2A	109.1	O1—C5—C4	122.8 (4)
C1—C2—H2B	109.1	N1—C5—C4	117.9 (4)
C1—C2—C3	112.5 (3)

Cu1—S1—C1—N1	−165.4 (3)	C1—C2—C3—C4	52.5 (5)
Cu1—S1—C1—C2	13.3 (4)	C2—C3—C4—C5	−52.7 (5)
S1—C1—C2—C3	155.5 (3)	C3—C4—C5—O1	−154.2 (5)
N1—C1—C2—C3	−25.9 (5)	C3—C4—C5—N1	26.9 (6)
C1—N1—C5—O1	−177.4 (4)	C5—N1—C1—S1	176.5 (4)
C1—N1—C5—C4	1.5 (7)	C5—N1—C1—C2	−2.2 (7)

Symmetry codes: (i) −x+1/2, −y+3/2, z−1/2; (ii) x, −y+1, z−1/2; (iii) x, −y+1, z+1/2; (iv) −x+1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^v	0.86 (2)	2.03 (2)	2.881 (5)	171 (5)

Symmetry code: (v) −x+1, −y+1, −z+2.

Poly[[(piperidine-2,6-dithione-κS)copper(I)]-µ₃-iodido] (IV) top

Crystal data top

[Cu₂I₂(C₅H₇NS₂)₂]	F(000) = 1264
M_r = 671.35	D_x = 1.952 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 13.2866 (9) Å	Cell parameters from 9761 reflections
b = 11.6974 (13) Å	θ = 3.4–73.6°
c = 14.8089 (9) Å	µ = 26.87 mm⁻¹
β = 96.998 (6)°	T = 100 K
V = 2284.4 (3) Å³	Block, red
Z = 4	0.22 × 0.13 × 0.09 mm

Data collection top

Bruker SMART APEXII area detector diffractometer	4597 independent reflections
Radiation source: sealed X-ray tube, Siemens, K FFCU 2K 90	4236 reflections with I > 2σ(I)
Equatorially mounted graphite monochromator	R_int = 0.063
Detector resolution: 7.9 pixels mm^-1	θ_max = 73.6°, θ_min = 3.4°
0.60° ω and 0.6° φ scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −14→14
T_min = 0.009, T_max = 0.094	l = −18→18
78133 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0963P)² + 0.866P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4597 reflections	Δρ_max = 1.58 e Å⁻³
181 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I2	0.55860 (2)	0.62760 (3)	0.40198 (2)	0.04041 (13)
I1	−0.04785 (2)	0.16932 (3)	0.55075 (2)	0.04179 (13)
Cu1	0.09352 (5)	0.01033 (6)	0.55762 (5)	0.03868 (18)
Cu2	0.50067 (5)	0.41451 (7)	0.43516 (5)	0.04040 (19)
S4	0.88076 (9)	0.04448 (10)	0.29165 (8)	0.0381 (3)
S2	0.38476 (10)	0.38690 (11)	0.31034 (9)	0.0419 (3)
S3	0.64474 (10)	0.30477 (12)	0.45389 (8)	0.0444 (3)
S1	0.24194 (9)	0.09681 (11)	0.52729 (8)	0.0410 (3)
N1	0.2946 (3)	0.2359 (4)	0.4050 (3)	0.0400 (9)
H1	0.341595	0.255812	0.449306	0.048*
N2	0.7560 (3)	0.1895 (4)	0.3534 (3)	0.0393 (9)
H2	0.784079	0.164625	0.406656	0.047*
C6	0.6808 (4)	0.2704 (4)	0.3544 (3)	0.0392 (10)
C1	0.2258 (4)	0.1562 (5)	0.4253 (3)	0.0399 (10)
C10	0.7913 (4)	0.1441 (4)	0.2793 (4)	0.0373 (10)
C5	0.2980 (4)	0.2881 (4)	0.3228 (4)	0.0400 (10)
C2	0.1396 (4)	0.1307 (5)	0.3541 (4)	0.0451 (12)
H2A	0.077033	0.121868	0.383553	0.054*
H2B	0.152702	0.056988	0.324839	0.054*
C9	0.7453 (4)	0.1855 (5)	0.1882 (3)	0.0414 (11)
H9A	0.687396	0.135704	0.165575	0.050*
H9B	0.796127	0.180538	0.144760	0.050*
C7	0.6364 (5)	0.3190 (5)	0.2646 (4)	0.0473 (12)
H7A	0.620041	0.400624	0.272580	0.057*
H7B	0.572524	0.278409	0.243395	0.057*
C4	0.2216 (4)	0.2518 (5)	0.2464 (4)	0.0449 (11)
H4A	0.247023	0.184112	0.216075	0.054*
H4B	0.211015	0.314198	0.200990	0.054*
C8	0.7087 (5)	0.3083 (5)	0.1928 (4)	0.0480 (12)
H8A	0.673595	0.331533	0.132807	0.058*
H8B	0.767460	0.359753	0.208203	0.058*
C3	0.1218 (4)	0.2229 (5)	0.2805 (4)	0.0474 (12)
H3A	0.072927	0.194853	0.229493	0.057*
H3B	0.092969	0.292195	0.305907	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I2	0.0431 (2)	0.0411 (2)	0.0377 (2)	−0.00315 (12)	0.00764 (14)	0.00019 (12)
I1	0.0442 (2)	0.0404 (2)	0.0395 (2)	0.00544 (12)	0.00003 (14)	−0.00445 (12)
Cu1	0.0398 (4)	0.0393 (4)	0.0368 (4)	0.0010 (3)	0.0043 (3)	0.0020 (3)
Cu2	0.0397 (4)	0.0416 (4)	0.0404 (4)	0.0001 (3)	0.0066 (3)	−0.0006 (3)
S4	0.0389 (6)	0.0400 (6)	0.0356 (5)	0.0026 (4)	0.0055 (4)	0.0004 (5)
S2	0.0425 (6)	0.0427 (6)	0.0406 (6)	−0.0043 (5)	0.0054 (5)	0.0042 (5)
S3	0.0462 (7)	0.0530 (7)	0.0346 (6)	0.0106 (5)	0.0069 (5)	0.0011 (5)
S1	0.0416 (6)	0.0460 (7)	0.0352 (6)	−0.0036 (5)	0.0034 (5)	0.0044 (5)
N1	0.039 (2)	0.044 (2)	0.0367 (19)	−0.0026 (17)	0.0041 (16)	0.0006 (18)
N2	0.039 (2)	0.044 (2)	0.0346 (19)	0.0019 (17)	0.0018 (16)	0.0039 (17)
C6	0.041 (2)	0.038 (2)	0.038 (2)	0.0000 (19)	0.0046 (19)	0.003 (2)
C1	0.041 (3)	0.044 (3)	0.035 (2)	0.000 (2)	0.004 (2)	0.001 (2)
C10	0.036 (2)	0.037 (2)	0.039 (2)	−0.0020 (18)	0.0048 (19)	0.001 (2)
C5	0.038 (2)	0.042 (3)	0.040 (2)	0.001 (2)	0.0050 (19)	−0.001 (2)
C2	0.047 (3)	0.051 (3)	0.037 (3)	−0.008 (2)	0.003 (2)	0.003 (2)
C9	0.046 (3)	0.044 (3)	0.034 (2)	0.005 (2)	0.006 (2)	−0.001 (2)
C7	0.055 (3)	0.049 (3)	0.037 (3)	0.013 (2)	0.004 (2)	0.002 (2)
C4	0.049 (3)	0.045 (3)	0.040 (3)	−0.005 (2)	0.004 (2)	0.006 (2)
C8	0.062 (3)	0.047 (3)	0.035 (2)	0.012 (3)	0.010 (2)	0.006 (2)
C3	0.042 (3)	0.057 (3)	0.042 (3)	−0.004 (2)	0.001 (2)	0.002 (2)

Geometric parameters (Å, º) top

I1—Cu1	2.6365 (8)	C1—C2	1.490 (7)
I1—Cu1ⁱ	2.6687 (8)	C10—C9	1.491 (7)
I2—Cu2	2.6719 (8)	C5—C4	1.487 (7)
I2—Cu2ⁱⁱ	2.6724 (8)	C2—H2A	0.9900
Cu1—S4ⁱⁱⁱ	2.3075 (13)	C2—H2B	0.9900
Cu1—S1	2.3086 (14)	C2—C3	1.531 (8)
Cu2—S2	2.2802 (15)	C9—H9A	0.9900
Cu2—S3	2.2933 (15)	C9—H9B	0.9900
S4—C10	1.659 (5)	C9—C8	1.521 (7)
S2—C5	1.659 (5)	C7—H7A	0.9900
S3—C6	1.654 (5)	C7—H7B	0.9900
S1—C1	1.652 (5)	C7—C8	1.522 (8)
N1—H1	0.8800	C4—H4A	0.9900
N1—C1	1.365 (7)	C4—H4B	0.9900
N1—C5	1.367 (7)	C4—C3	1.514 (8)
N2—H2	0.8800	C8—H8A	0.9900
N2—C6	1.378 (7)	C8—H8B	0.9900
N2—C10	1.354 (7)	C3—H3A	0.9900
C6—C7	1.498 (7)	C3—H3B	0.9900

Cu2—I2—Cu2ⁱⁱ	62.54 (3)	C1—C2—H2A	108.8
Cu1—I1—Cu1ⁱ	64.94 (3)	C1—C2—H2B	108.8
I1—Cu1—I1ⁱ	115.06 (3)	C1—C2—C3	113.7 (5)
S4ⁱⁱⁱ—Cu1—I1	104.72 (4)	H2A—C2—H2B	107.7
S4ⁱⁱⁱ—Cu1—I1ⁱ	111.04 (4)	C3—C2—H2A	108.8
S4ⁱⁱⁱ—Cu1—S1	106.30 (5)	C3—C2—H2B	108.8
S1—Cu1—I1ⁱ	111.41 (4)	C10—C9—H9A	109.4
S1—Cu1—I1	107.75 (4)	C10—C9—H9B	109.4
I2—Cu2—I2ⁱⁱ	117.46 (3)	C10—C9—C8	111.3 (4)
S2—Cu2—I2ⁱⁱ	117.47 (4)	H9A—C9—H9B	108.0
S2—Cu2—I2	99.46 (4)	C8—C9—H9A	109.4
S2—Cu2—S3	119.35 (6)	C8—C9—H9B	109.4
S3—Cu2—I2ⁱⁱ	96.95 (4)	C6—C7—H7A	109.2
S3—Cu2—I2	106.83 (5)	C6—C7—H7B	109.2
C10—S4—Cu1ⁱⁱⁱ	108.78 (18)	C6—C7—C8	112.1 (5)
C5—S2—Cu2	114.75 (19)	H7A—C7—H7B	107.9
C6—S3—Cu2	110.88 (19)	C8—C7—H7A	109.2
C1—S1—Cu1	110.1 (2)	C8—C7—H7B	109.2
C1—N1—H1	116.7	C5—C4—H4A	109.5
C1—N1—C5	126.6 (5)	C5—C4—H4B	109.5
C5—N1—H1	116.7	C5—C4—C3	110.7 (5)
C6—N2—H2	116.5	H4A—C4—H4B	108.1
C10—N2—H2	116.5	C3—C4—H4A	109.5
C10—N2—C6	127.0 (4)	C3—C4—H4B	109.5
N2—C6—S3	117.7 (4)	C9—C8—C7	109.9 (5)
N2—C6—C7	117.3 (4)	C9—C8—H8A	109.7
C7—C6—S3	125.0 (4)	C9—C8—H8B	109.7
N1—C1—S1	118.2 (4)	C7—C8—H8A	109.7
N1—C1—C2	117.3 (5)	C7—C8—H8B	109.7
C2—C1—S1	124.5 (4)	H8A—C8—H8B	108.2
N2—C10—S4	120.0 (4)	C2—C3—H3A	109.8
N2—C10—C9	117.5 (4)	C2—C3—H3B	109.8
C9—C10—S4	122.5 (4)	C4—C3—C2	109.2 (5)
N1—C5—S2	120.6 (4)	C4—C3—H3A	109.8
N1—C5—C4	117.2 (4)	C4—C3—H3B	109.8
C4—C5—S2	122.2 (4)	H3A—C3—H3B	108.3

Cu1ⁱⁱⁱ—S4—C10—N2	8.2 (5)	N2—C6—C7—C8	−23.4 (7)
Cu1ⁱⁱⁱ—S4—C10—C9	−170.5 (4)	N2—C10—C9—C8	29.6 (7)
Cu1—S1—C1—N1	162.9 (4)	C6—N2—C10—S4	−178.4 (4)
Cu1—S1—C1—C2	−15.7 (5)	C6—N2—C10—C9	0.4 (8)
Cu2—S2—C5—N1	4.8 (5)	C6—C7—C8—C9	51.7 (7)
Cu2—S2—C5—C4	−174.9 (4)	C1—N1—C5—S2	177.9 (4)
Cu2—S3—C6—N2	−169.5 (3)	C1—N1—C5—C4	−2.4 (8)
Cu2—S3—C6—C7	9.3 (5)	C1—C2—C3—C4	48.8 (7)
S4—C10—C9—C8	−151.7 (4)	C10—N2—C6—S3	175.3 (4)
S2—C5—C4—C3	−145.6 (4)	C10—N2—C6—C7	−3.7 (8)
S3—C6—C7—C8	157.7 (4)	C10—C9—C8—C7	−54.8 (6)
S1—C1—C2—C3	160.4 (4)	C5—N1—C1—S1	175.1 (4)
N1—C1—C2—C3	−18.2 (7)	C5—N1—C1—C2	−6.3 (8)
N1—C5—C4—C3	34.7 (7)	C5—C4—C3—C2	−56.3 (6)

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I2ⁱⁱ	0.88	2.79	3.628 (4)	161
N2—H2···I1^iv	0.88	2.90	3.679 (4)	149

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iv) x+1, y, z.

Poly[[(µ-isoindoline-1,3-dithione-κ²S:S)copper(I)]-µ₃-iodido] (V) top

Crystal data top

[CuI(C₈H₅NS₂)]	F(000) = 696
M_r = 369.69	D_x = 2.492 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 15.174 (5) Å	Cell parameters from 4507 reflections
b = 4.1188 (16) Å	θ = 2.6–31.9°
c = 15.785 (6) Å	µ = 5.72 mm⁻¹
β = 92.98 (2)°	T = 100 K
V = 985.2 (6) Å³	Block, black
Z = 4	0.30 × 0.02 × 0.01 mm

Data collection top

Bruker APEXII Quazar diffractometer	3603 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	3226 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.041
Detector resolution: 7.9 pixels mm^-1	θ_max = 33.2°, θ_min = 2.6°
0.5° ω and 0.5° φ scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −6→6
T_min = 0.322, T_max = 0.404	l = −23→23
11871 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0417P)² + 7.0163P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.089	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 3.17 e Å⁻³
3603 reflections	Δρ_min = −1.13 e Å⁻³
118 parameters	Absolute structure: Flack x determined using 1438 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.034 (12)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.68957 (2)	0.10931 (10)	0.74974 (2)	0.01374 (11)
Cu1	0.59491 (6)	0.5992 (2)	0.69164 (6)	0.0146 (2)
S1	0.60747 (14)	0.6607 (5)	0.54996 (12)	0.0139 (3)
S2	0.46550 (14)	0.2757 (5)	0.25028 (12)	0.0146 (3)
N1	0.5450 (5)	0.4774 (16)	0.3969 (4)	0.0133 (12)
H1	0.587624	0.579000	0.371951	0.016*
C1	0.5382 (5)	0.4700 (18)	0.4850 (5)	0.0122 (13)
C2	0.4596 (5)	0.2691 (18)	0.4975 (5)	0.0124 (14)
C3	0.4197 (5)	0.1812 (19)	0.5712 (5)	0.0147 (14)
H3	0.442699	0.252848	0.625113	0.018*
C4	0.3448 (5)	−0.015 (2)	0.5639 (5)	0.0148 (14)
H4	0.316667	−0.082004	0.613403	0.018*
C5	0.3106 (5)	−0.115 (2)	0.4828 (5)	0.0165 (15)
H5	0.259718	−0.249734	0.478913	0.020*
C6	0.3493 (5)	−0.0227 (18)	0.4093 (5)	0.0128 (13)
H6	0.325668	−0.090075	0.355269	0.015*
C7	0.4244 (5)	0.1733 (18)	0.4172 (5)	0.0125 (13)
C8	0.4795 (5)	0.3123 (19)	0.3538 (5)	0.0118 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0131 (2)	0.01109 (17)	0.0169 (2)	−0.0009 (2)	−0.00081 (15)	−0.0008 (2)
Cu1	0.0155 (5)	0.0162 (5)	0.0122 (5)	−0.0008 (4)	0.0004 (4)	−0.0010 (4)
S1	0.0141 (9)	0.0150 (8)	0.0124 (8)	0.0001 (6)	0.0003 (7)	−0.0011 (6)
S2	0.0132 (8)	0.0185 (9)	0.0120 (8)	−0.0011 (7)	−0.0002 (7)	−0.0017 (7)
N1	0.014 (3)	0.014 (3)	0.012 (3)	0.001 (2)	0.001 (2)	0.001 (2)
C1	0.012 (3)	0.012 (3)	0.013 (3)	0.003 (2)	0.000 (3)	0.002 (3)
C2	0.012 (4)	0.009 (3)	0.017 (3)	0.006 (3)	0.002 (3)	0.000 (2)
C3	0.014 (3)	0.013 (3)	0.017 (3)	0.002 (3)	0.002 (3)	0.001 (3)
C4	0.010 (3)	0.018 (3)	0.017 (4)	0.001 (3)	0.003 (3)	0.002 (3)
C5	0.012 (3)	0.018 (4)	0.019 (4)	−0.002 (3)	−0.003 (3)	0.001 (3)
C6	0.011 (3)	0.011 (3)	0.017 (3)	0.000 (2)	−0.001 (3)	0.001 (3)
C7	0.015 (3)	0.009 (3)	0.014 (3)	0.002 (2)	0.002 (3)	0.001 (2)
C8	0.011 (3)	0.013 (3)	0.012 (3)	0.003 (2)	0.002 (3)	0.000 (2)

Geometric parameters (Å, º) top

I1—Cu1	2.6152 (13)	C2—C7	1.405 (11)
I1—Cu1ⁱ	2.6798 (13)	C3—H3	0.9500
Cu1—S1	2.269 (2)	C3—C4	1.394 (12)
Cu1—S2ⁱⁱ	2.273 (2)	C4—H4	0.9500
S1—C1	1.632 (8)	C4—C5	1.417 (12)
S2—C8	1.645 (7)	C5—H5	0.9500
N1—H1	0.8800	C5—C6	1.380 (11)
N1—C1	1.400 (10)	C6—H6	0.9500
N1—C8	1.357 (10)	C6—C7	1.396 (11)
C1—C2	1.473 (11)	C7—C8	1.455 (11)
C2—C3	1.388 (11)

Cu1—I1—Cu1ⁱ	102.12 (4)	C2—C3—H3	120.9
I1—Cu1—I1ⁱⁱⁱ	102.12 (4)	C2—C3—C4	118.1 (8)
S1—Cu1—I1ⁱⁱⁱ	100.30 (6)	C4—C3—H3	120.9
S1—Cu1—I1	111.05 (6)	C3—C4—H4	120.0
S1—Cu1—S2ⁱⁱ	119.65 (8)	C3—C4—C5	120.1 (8)
S2ⁱⁱ—Cu1—I1ⁱⁱⁱ	98.16 (7)	C5—C4—H4	120.0
S2ⁱⁱ—Cu1—I1	120.16 (7)	C4—C5—H5	119.1
C1—S1—Cu1	118.8 (3)	C6—C5—C4	121.8 (8)
C8—S2—Cu1^iv	108.3 (3)	C6—C5—H5	119.1
C1—N1—H1	123.3	C5—C6—H6	121.1
C8—N1—H1	123.3	C5—C6—C7	117.7 (7)
C8—N1—C1	113.3 (7)	C7—C6—H6	121.1
N1—C1—S1	122.3 (6)	C2—C7—C8	107.7 (7)
N1—C1—C2	104.3 (7)	C6—C7—C2	120.9 (7)
C2—C1—S1	133.3 (6)	C6—C7—C8	131.4 (7)
C3—C2—C1	130.6 (7)	N1—C8—S2	126.7 (6)
C3—C2—C7	121.4 (7)	N1—C8—C7	106.6 (6)
C7—C2—C1	108.0 (7)	C7—C8—S2	126.7 (6)

Cu1—S1—C1—N1	−175.6 (5)	C2—C7—C8—S2	−179.1 (6)
Cu1—S1—C1—C2	5.3 (9)	C2—C7—C8—N1	1.0 (8)
Cu1^iv—S2—C8—N1	18.3 (8)	C3—C2—C7—C6	−2.0 (11)
Cu1^iv—S2—C8—C7	−161.5 (6)	C3—C2—C7—C8	178.2 (7)
S1—C1—C2—C3	0.4 (13)	C3—C4—C5—C6	−0.2 (12)
S1—C1—C2—C7	178.6 (6)	C4—C5—C6—C7	0.4 (12)
N1—C1—C2—C3	−178.9 (8)	C5—C6—C7—C2	0.7 (11)
N1—C1—C2—C7	−0.6 (8)	C5—C6—C7—C8	−179.6 (8)
C1—N1—C8—S2	178.7 (6)	C6—C7—C8—S2	1.1 (12)
C1—N1—C8—C7	−1.5 (9)	C6—C7—C8—N1	−178.7 (8)
C1—C2—C3—C4	−179.8 (8)	C7—C2—C3—C4	2.1 (11)
C1—C2—C7—C6	179.5 (7)	C8—N1—C1—S1	−178.0 (6)
C1—C2—C7—C8	−0.2 (8)	C8—N1—C1—C2	1.3 (8)
C2—C3—C4—C5	−1.0 (12)

Symmetry codes: (i) x, y−1, z; (ii) x, −y+1, z+1/2; (iii) x, y+1, z; (iv) x, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1^iv	0.88	2.84	3.692 (7)	163

Symmetry code: (iv) x, −y+1, z−1/2.

Selected bond lengths for structures I–V top

	I^a		II^b		III^c		IV^d		V^e
Cu—I	I1—Cu1	2.6261 (6)	I1—Cu1	2.6451 (6)	I1—Cu1	2.6264 (11)	I1—Cu1	2.6365 (8)	I1—Cu1	2.6152 (13)
	I1—Cu1ⁱ	2.6321 (7)	I1—Cu2ⁱ	2.7017 (7)	I1—Cu1ⁱ	2.6709 (12)	I1—Cu1ⁱ	2.6687 (8)	I1—Cu1ⁱ	2.6798 (13)
			I1—Cu2	2.7250 (6)	I1—Cu1ⁱⁱ	2.6342 (10)	I2—Cu2	2.6719 (8)
			I2—Cu1	2.7796 (6)			I2—Cu2ⁱⁱ	2.6724 (8)
			I2—Cu1ⁱ	2.6542 (6)
			I2—Cu2	2.6456 (6)
Cu···Cu	Cu1—Cu1ⁱ	2.7274 (6)	Cu1—Cu1ⁱ	2.8150 (11)
			Cu1—Cu2	2.7864 (8)
			Cu1—Cu2ⁱ	2.7106 (8)
			Cu2—Cu2ⁱ	2.5803 (10)
Cu—S	Cu1—S1	2.3205 (6)	Cu1–S1	2.2869 (10)	Cu1—S1	2.2827 (15)	Cu1—S1	2.3086 (14)	Cu1—S1	2.269 (2)
							Cu1—S4ⁱⁱⁱ	2.3075 (13)	Cu1—S2ⁱⁱ	2.273 (2)
							Cu2—S2	2.2802 (15)
							Cu2—S3	2.2933 (15)
Cu—N	Cu1—N2	2.0225 (10)	Cu2—N2	1.974 (3)

Symmetry codes: (a) (i) -x + 1, -y + 1, -z for I; (b) (i) -x + 1, y, -z + 1/2 for II; (c) (i) -x + 1/2, -y + 3/2, z - 1/2 and (ii) x, -y + 1, z - 1/2 for III; (d) (i) -x, -y, -z + 1; (ii) -x + 1, -y + 1, -z + 1 and (iii) -x + 1, -y, -z + 1 for IV; (e) (i) x, y - 1, z and (ii) x, -y + 1, z + 1/2 for V.

Hydrogen bonding geometries for I–V top

	D—H···A	D—H	H···A	D···A	D—H···A
I^a	N1—H1···I1ⁱ	0.857 (12)	2.845 (13)	3.6980 (12)	173.8 (13)
II	N1—H1···I2	0.870 (19)	2.81 (2)	3.672 (3)	170 (4)
III^b	N1—H1···O1ⁱⁱⁱ	0.86 (2)	2.03 (2)	2.881 (5)	171 (5)
IV^c	N1—H1···I2ⁱⁱ	0.88	2.79	3.628 (4)	160.9
	N2—H2···I1^iv	0.88	2.90	3.679 (4)	149.2
V^d	N1—H1···I1ⁱⁱⁱ	0.88	2.84	3.692 (7)	163.2

Symmetry codes: (a) (i) -x + 1, -y + 1, -z for I; (b) (iii) -x + 1, -y + 1, -z + 2 for III; (c) (ii) -x + 1, -y + 1, -z + 1 and (iv) x + 1, y, z for IV; (d) (iii) x, -y + 1, z - 1/2 for IV.

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Structural diversity in copper(I) iodide complexes with 6-thioxopiperidin-2-one, piperidine-2,6-di­thione and isoindoline-1,3-di­thione ligands

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Structural diversity in copper(I) iodide complexes with 6-thioxopiperidin-2-one, piperidine-2,6-dithione and isoindoline-1,3-dithione ligands