Bis[N,N′-bis­(3,3-diphenyl­prop-2-enyl­idene)ethane-1,2-diamine-κ²N,N′]copper(I) triiodide

The title complex, [Cu(C₃₂H₂₈N₂)₂]I₃, contains cations having Cu^I coordinated by four N atoms of two N,N′-bis­(3,3-diphenyl­prop-2-enyl­idene)ethane-1,2-diamine (Phca₂en) ligands in a distorted tetra­hedral fashion and isolated linear I₃⁻ anions. The Phca₂en ligand adopts a Z,Z conformation and acts as a bidentate ligand coordinating via two N atoms to the Cu atom. The Cu and central I atoms are located on twofold axes.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.069
• Data-to-parameter ratio = 28.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.61 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.63
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.09 Ratio

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      0.628
            Tmax scaled      0.516 Tmin scaled      0.426
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           32.01
           From the CIF: _reflns_number_total               4735
           Count of symmetry unique reflns         2686
           Completeness (_total/calc)            176.28%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2049
           Fraction of Friedel pairs measured     0.763
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[N,N'-bis(3,3-diphenylprop-2-enylidene)ethane-1,2-diamine-κ²N,N']copper(I) triiodide

Crystal data

[Cu(C32H28N2)2]I3	Dx = 1.558 Mg m^−3
Mr = 1325.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4n2	Cell parameters from 11035 reflections
Hall symbol: P -4 -2n	θ = 2.7–32.0°
a = 17.1304 (7) Å	µ = 2.07 mm^−1
c = 9.6273 (4) Å	T = 180 K
V = 2825.1 (2) Å^3	Prism, dark red
Z = 2	0.4 × 0.38 × 0.32 mm
F(000) = 1312

Data collection

Oxford XCALIBUR diffractometer	4735 independent reflections
Radiation source: fine-focus sealed tube	3587 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.2632 pixels mm^-1	θmax = 32.0°, θmin = 2.7°
φ and ω scans	h = −24→25
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −25→24
Tmin = 0.678, Tmax = 0.821	l = −13→13
29420 measured reflections

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)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0211P)^2 + 1.9967P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4735 reflections	Δρmax = 1.04 e Å^−3
165 parameters	Δρmin = −0.73 e Å^−3
0 restraints	Absolute structure: Flack (1983) and Bernardinelli & Flack (1985), using 2109 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.031 (18)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C1	−0.10339 (13)	0.37530 (14)	0.1759 (3)	0.0367 (6)
H1A	−0.1095	0.3184	0.1616	0.044*
H1B	−0.1383	0.4028	0.1100	0.044*
C11	0.02211 (14)	0.34988 (14)	0.0877 (3)	0.0271 (5)
H11	0.0026	0.2999	0.0628	0.033*
C12	0.10134 (13)	0.37033 (13)	0.0531 (2)	0.0274 (5)
H12	0.1151	0.4240	0.0555	0.033*
C13	0.15754 (12)	0.31876 (12)	0.0176 (2)	0.0236 (5)
C131	0.14578 (14)	0.23369 (14)	0.0368 (3)	0.0252 (5)
C132	0.11750 (15)	0.20465 (15)	0.1617 (3)	0.0319 (5)
H132	0.1057	0.2397	0.2354	0.038*
C133	0.10618 (18)	0.12488 (16)	0.1803 (3)	0.0397 (7)
H133	0.0868	0.1055	0.2662	0.048*
C134	0.12333 (19)	0.07372 (16)	0.0727 (3)	0.0432 (7)
H134	0.1154	0.0192	0.0843	0.052*
C135	0.15180 (19)	0.10206 (17)	−0.0506 (3)	0.0367 (7)
H135	0.1635	0.0668	−0.1238	0.044*
C136	0.16364 (14)	0.18091 (15)	−0.0697 (3)	0.0289 (5)
H136	0.1840	0.1995	−0.1554	0.035*
C141	0.23381 (15)	0.34646 (15)	−0.0324 (3)	0.0294 (5)
C142	0.30174 (16)	0.3029 (2)	−0.0094 (3)	0.0423 (6)
H142	0.2987	0.2528	0.0327	0.051*
C143	0.3736 (2)	0.3332 (3)	−0.0484 (5)	0.0687 (15)
H143	0.4195	0.3035	−0.0323	0.082*
C144	0.3795 (3)	0.4043 (3)	−0.1091 (5)	0.0850 (18)
H144	0.4293	0.4249	−0.1326	0.102*
C145	0.3133 (3)	0.4465 (2)	−0.1362 (4)	0.0736 (14)
H145	0.3174	0.4959	−0.1804	0.088*
C146	0.2405 (2)	0.41798 (18)	−0.0998 (3)	0.0466 (8)
H146	0.1950	0.4473	−0.1209	0.056*
N1	−0.02260 (11)	0.39815 (11)	0.1515 (2)	0.0246 (4)
Cu1	0.0000	0.5000	0.2500	0.02255 (9)
I1	0.0000	0.5000	0.7500	0.04172 (8)
I2	−0.120456 (12)	0.379544 (12)	0.7500	0.06406 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0203 (11)	0.0235 (12)	0.0664 (16)	−0.0043 (10)	−0.0029 (10)	−0.0112 (11)
C11	0.0256 (11)	0.0177 (10)	0.0380 (13)	0.0004 (8)	0.0015 (9)	−0.0054 (9)
C12	0.0292 (11)	0.0202 (10)	0.0327 (11)	0.0004 (9)	0.0030 (9)	−0.0029 (9)
C13	0.0256 (10)	0.0221 (10)	0.0231 (10)	0.0006 (9)	0.0010 (8)	−0.0030 (8)
C131	0.0217 (10)	0.0240 (11)	0.0298 (11)	0.0057 (9)	−0.0036 (9)	−0.0026 (9)
C132	0.0380 (14)	0.0307 (12)	0.0271 (12)	0.0040 (11)	−0.0018 (11)	0.0007 (10)
C133	0.0483 (17)	0.0347 (14)	0.0362 (14)	0.0007 (12)	−0.0022 (12)	0.0127 (11)
C134	0.0538 (18)	0.0224 (12)	0.0534 (18)	0.0035 (12)	−0.0163 (15)	0.0073 (12)
C135	0.0412 (16)	0.0259 (13)	0.0431 (16)	0.0102 (13)	−0.0096 (13)	−0.0082 (12)
C136	0.0272 (12)	0.0280 (12)	0.0315 (12)	0.0067 (10)	−0.0015 (10)	−0.0027 (10)
C141	0.0298 (12)	0.0323 (12)	0.0262 (11)	−0.0042 (10)	0.0041 (10)	−0.0101 (10)
C142	0.0287 (14)	0.063 (2)	0.0355 (13)	0.0025 (12)	−0.0010 (12)	−0.0163 (14)
C143	0.0289 (17)	0.123 (4)	0.055 (2)	−0.016 (2)	0.0049 (15)	−0.047 (3)
C144	0.059 (3)	0.122 (4)	0.075 (3)	−0.058 (3)	0.038 (2)	−0.059 (3)
C145	0.095 (3)	0.059 (2)	0.067 (2)	−0.046 (2)	0.049 (2)	−0.0301 (19)
C146	0.061 (2)	0.0331 (15)	0.0451 (16)	−0.0114 (14)	0.0251 (15)	−0.0098 (12)
N1	0.0206 (9)	0.0205 (9)	0.0326 (10)	0.0005 (7)	0.0008 (8)	−0.0021 (8)
Cu1	0.01616 (12)	0.01616 (12)	0.0353 (2)	0.00021 (17)	0.000	0.000
I1	0.04703 (12)	0.04703 (12)	0.03111 (14)	0.00530 (14)	0.000	0.000
I2	0.07092 (13)	0.07092 (13)	0.05035 (15)	−0.01943 (15)	0.00613 (19)	−0.00613 (19)

Geometric parameters (Å, º)

C1—N1	1.457 (3)	C134—H134	0.9500
C1—C1^i	1.518 (6)	C135—C136	1.378 (4)
C1—H1A	0.9900	C135—H135	0.9500
C1—H1B	0.9900	C136—H136	0.9500
C11—N1	1.284 (3)	C141—C146	1.391 (4)
C11—C12	1.441 (3)	C141—C142	1.400 (4)
C11—H11	0.9500	C142—C143	1.388 (5)
C12—C13	1.351 (3)	C142—H142	0.9500
C12—H12	0.9500	C143—C144	1.355 (8)
C13—C141	1.471 (3)	C143—H143	0.9500
C13—C131	1.483 (3)	C144—C145	1.369 (7)
C131—C132	1.389 (4)	C144—H144	0.9500
C131—C136	1.401 (3)	C145—C146	1.385 (5)
C132—C133	1.392 (4)	C145—H145	0.9500
C132—H132	0.9500	C146—H146	0.9500
C133—C134	1.389 (4)	N1—Cu1	2.0232 (19)
C133—H133	0.9500	Cu1—N1^ii	2.0232 (19)
C134—C135	1.371 (5)	I1—I2	2.9182 (3)
N1—C1—C1^i	108.37 (18)	C131—C136—H136	119.9
N1—C1—H1A	110.0	C146—C141—C142	118.3 (3)
N1—C1—H1B	110.0	C146—C141—C13	120.7 (3)
H1A—C1—H1B	108.4	C142—C141—C13	121.0 (2)
N1—C11—C12	121.1 (2)	C143—C142—C141	119.7 (4)
N1—C11—H11	119.5	C143—C142—H142	120.2
C12—C11—H11	119.5	C141—C142—H142	120.2
C13—C12—C11	124.8 (2)	C144—C143—C142	121.3 (4)
C13—C12—H12	117.6	C144—C143—H143	119.4
C11—C12—H12	117.6	C142—C143—H143	119.4
C12—C13—C141	120.3 (2)	C143—C144—C145	119.6 (3)
C12—C13—C131	121.0 (2)	C143—C144—H144	120.2
C141—C13—C131	118.6 (2)	C145—C144—H144	120.2
C132—C131—C136	118.6 (2)	C144—C145—C146	120.8 (4)
C132—C131—C13	120.5 (2)	C144—C145—H145	119.6
C136—C131—C13	120.9 (2)	C146—C145—H145	119.6
C131—C132—C133	120.8 (3)	C145—C146—C141	120.2 (4)
C131—C132—H132	119.6	C145—C146—H146	119.9
C133—C132—H132	119.6	C141—C146—H146	119.9
C134—C133—C132	119.6 (3)	C11—N1—C1	118.1 (2)
C134—C133—H133	120.2	C11—N1—Cu1	131.74 (17)
C132—C133—H133	120.2	C1—N1—Cu1	109.75 (14)
C135—C134—C133	119.8 (3)	N1—Cu1—N1^ii	123.35 (11)
C135—C134—H134	120.1	N1—Cu1—N1^i	83.67 (11)
C133—C134—H134	120.1	N1^ii—Cu1—N1^i	124.09 (12)
C134—C135—C136	121.0 (3)	N1—Cu1—N1^iii	124.09 (12)
C134—C135—H135	119.5	N1^ii—Cu1—N1^iii	83.67 (11)
C136—C135—H135	119.5	N1^i—Cu1—N1^iii	123.35 (11)
C135—C136—C131	120.2 (3)	I2^iii—I1—I2	180.0
C135—C136—H136	119.9

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