Di-μ-iodo-bis­{[N,N′-bis­(3,3-diphenyl­prop-2-enyl­idene)propane-1,3-diamine-κ²N,N′]copper(I)}

The title compound, [Cu₂I₂(C₃₃H₃₀N₂)₂], is a centrosymmetric dinuclear copper(I) complex in which the Cu atom is coordinated by the bidentate N,N′-bis­(3,3-diphenyl­prop-2-enyl­idene)propane-1,3-diamine ligands and bridged by two I atoms. The distance between the two Cu atoms is 3.372 (2) Å and the coordination geometry is distorted tetra­hedral. Both coordinated diimine ligands adopt an E,E conformation.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.034
• wR factor = 0.068
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  I1     -   Cu1_a   ..      38.08 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.687     0.745
            Tmin and Tmax expected:      0.693     0.832
            RR =      1.106
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.11
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.12
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  I1     -   Cu1     ..       7.86 su

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      1.117
            Tmax scaled      0.832 Tmin scaled      0.767

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: IPDS (Stoe & Cie, 2000); cell refinement: IPDS; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Di-µ-iodo-bis{[N,N'-bis(3,3-diphenylprop-2-enylidene)propane-1,3-diamine- κ²N,N']copper(I)}

Crystal data

[Cu2I2(C33H30N2)2]	F(000) = 1296
Mr = 1290.06	Dx = 1.477 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8000 reflections
a = 9.8335 (7) Å	θ = 2.3–26.0°
b = 16.7979 (15) Å	µ = 1.84 mm^−1
c = 17.7501 (13) Å	T = 180 K
β = 98.348 (9)°	Prism, orange
V = 2900.9 (4) Å^3	0.27 × 0.17 × 0.1 mm
Z = 2

Data collection

Stoe IPDS diffractometer	5626 independent reflections
Radiation source: fine-focus sealed tube	3715 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −12→12
Tmin = 0.687, Tmax = 0.745	k = −20→20
28088 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0323P)^2] where P = (Fo^2 + 2Fc^2)/3
5626 reflections	(Δ/σ)max = 0.004
334 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.62 e Å^−3

Special details

Experimental. The data were collected on a Stoe Imaging Plate Diffraction System (IPDS). The crystal-to-detector distance was 80 mm. 143 frames (3 min per frame) were obtained with 0 < φ < 200.2° and with the crystals rotated through 1.4° in φ. Coverage of the unique set was over 99.3% complete to at least 24.11°. Crystal decay was monitored by measuring 200 reflections per frame.

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
Cu1	0.88415 (5)	0.07061 (3)	0.49075 (2)	0.03528 (13)
I1	1.14892 (3)	0.089234 (2)	0.49242 (1)	0.03327 (8)
N1	0.7429 (3)	0.0979 (2)	0.39730 (15)	0.0341 (7)
N2	0.7830 (3)	0.11325 (19)	0.57661 (15)	0.0336 (8)
C1	0.6000 (4)	0.0962 (3)	0.41305 (18)	0.0413 (10)
H1A	0.5741	0.0404	0.4220	0.050*
H1B	0.5386	0.1158	0.3677	0.050*
C2	0.6311 (4)	0.1096 (3)	0.5582 (2)	0.0434 (11)
H2A	0.5899	0.1378	0.5983	0.052*
H2B	0.6015	0.0533	0.5583	0.052*
C3	0.5778 (4)	0.1463 (3)	0.4817 (2)	0.0448 (11)
H3A	0.6233	0.1984	0.4780	0.054*
H3B	0.4781	0.1563	0.4794	0.054*
C11	0.7582 (4)	0.1069 (2)	0.32704 (19)	0.0369 (10)
H11	0.6786	0.1151	0.2906	0.044*
C12	0.8892 (4)	0.1050 (2)	0.30114 (19)	0.0381 (10)
H12	0.9685	0.1039	0.3387	0.046*
C13	0.9091 (4)	0.1045 (2)	0.22745 (19)	0.0360 (10)
C21	0.8311 (4)	0.1311 (2)	0.64550 (18)	0.0336 (9)
H21	0.7688	0.1443	0.6798	0.040*
C22	0.9750 (4)	0.1321 (2)	0.67259 (19)	0.0336 (9)
H22	1.0355	0.1215	0.6366	0.040*
C23	1.0325 (4)	0.1467 (2)	0.74491 (18)	0.0299 (9)
C131	0.7917 (4)	0.1122 (2)	0.16478 (18)	0.0343 (10)
C132	0.7216 (6)	0.1831 (3)	0.1484 (2)	0.0527 (13)
H132	0.7480	0.2290	0.1782	0.063*
C133	0.6141 (5)	0.1880 (3)	0.0894 (2)	0.0555 (13)
H133	0.5663	0.2369	0.0795	0.067*
C134	0.5757 (5)	0.1236 (3)	0.0452 (2)	0.0505 (12)
H134	0.5017	0.1275	0.0045	0.061*
C135	0.6443 (5)	0.0524 (3)	0.0596 (2)	0.0497 (12)
H135	0.6180	0.0072	0.0288	0.060*
C136	0.7512 (4)	0.0471 (3)	0.1187 (2)	0.0409 (10)
H136	0.7983	−0.0021	0.1282	0.049*
C141	1.0481 (4)	0.0939 (3)	0.2065 (2)	0.0410 (10)
C142	1.0794 (5)	0.1215 (3)	0.1362 (2)	0.0587 (14)
H142	1.0114	0.1484	0.1020	0.070*
C143	1.2085 (6)	0.1096 (4)	0.1168 (3)	0.0764 (18)
H143	1.2279	0.1280	0.0690	0.092*
C144	1.3107 (6)	0.0714 (4)	0.1653 (3)	0.0739 (17)
H144	1.3997	0.0641	0.1516	0.089*
C145	1.2803 (5)	0.0443 (3)	0.2337 (3)	0.0606 (13)
H145	1.3489	0.0173	0.2675	0.073*
C146	1.1529 (5)	0.0553 (3)	0.2543 (2)	0.0473 (11)
H146	1.1353	0.0363	0.3023	0.057*
C231	0.9475 (4)	0.1703 (2)	0.80467 (18)	0.0318 (9)
C232	0.9427 (5)	0.1220 (3)	0.8679 (2)	0.0415 (10)
H232	0.9940	0.0739	0.8735	0.050*
C233	0.8632 (5)	0.1441 (3)	0.9228 (2)	0.0453 (11)
H233	0.8584	0.1102	0.9652	0.054*
C234	0.7916 (5)	0.2138 (3)	0.9165 (2)	0.0449 (11)
H234	0.7388	0.2289	0.9549	0.054*
C235	0.7959 (4)	0.2620 (3)	0.8549 (2)	0.0433 (10)
H235	0.7459	0.3105	0.8505	0.052*
C236	0.8729 (4)	0.2403 (2)	0.79862 (19)	0.0382 (10)
H236	0.8744	0.2739	0.7557	0.046*
C241	1.1828 (4)	0.1418 (2)	0.76701 (18)	0.0327 (9)
C242	1.2653 (4)	0.0974 (3)	0.7247 (2)	0.0411 (10)
H242	1.2234	0.0670	0.6825	0.049*
C243	1.4056 (5)	0.0969 (3)	0.7431 (2)	0.0559 (12)
H243	1.4595	0.0664	0.7134	0.067*
C244	1.4694 (5)	0.1401 (3)	0.8041 (3)	0.0616 (14)
H244	1.5666	0.1395	0.8167	0.074*
C245	1.3901 (5)	0.1845 (3)	0.8467 (2)	0.0525 (12)
H245	1.4333	0.2153	0.8883	0.063*
C246	1.2496 (5)	0.1845 (2)	0.8296 (2)	0.0400 (10)
H246	1.1965	0.2139	0.8606	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0328 (3)	0.0511 (3)	0.0232 (2)	0.0026 (2)	0.00840 (18)	0.00236 (19)
I1	0.03248 (14)	0.04073 (14)	0.02890 (11)	−0.00125 (14)	0.01222 (9)	0.00348 (12)
N1	0.0393 (19)	0.041 (2)	0.0234 (14)	0.0015 (17)	0.0093 (13)	0.0023 (13)
N2	0.0286 (18)	0.049 (2)	0.0241 (15)	−0.0008 (15)	0.0059 (13)	0.0022 (13)
C1	0.030 (2)	0.069 (3)	0.0245 (17)	0.002 (2)	0.0001 (15)	0.0055 (19)
C2	0.027 (2)	0.076 (3)	0.0286 (19)	0.003 (2)	0.0084 (16)	0.0005 (19)
C3	0.029 (2)	0.072 (3)	0.035 (2)	0.011 (2)	0.0087 (17)	0.006 (2)
C11	0.045 (3)	0.042 (3)	0.0232 (17)	0.004 (2)	0.0028 (16)	0.0017 (16)
C12	0.042 (2)	0.046 (3)	0.0276 (18)	0.002 (2)	0.0069 (17)	−0.0008 (16)
C13	0.050 (3)	0.034 (2)	0.0253 (17)	−0.005 (2)	0.0107 (17)	−0.0025 (15)
C21	0.038 (2)	0.044 (2)	0.0211 (17)	0.005 (2)	0.0121 (16)	−0.0019 (15)
C22	0.036 (2)	0.043 (2)	0.0238 (18)	0.005 (2)	0.0122 (16)	−0.0011 (16)
C23	0.036 (2)	0.030 (2)	0.0250 (17)	0.0012 (18)	0.0083 (16)	0.0014 (15)
C131	0.043 (2)	0.043 (3)	0.0200 (17)	0.003 (2)	0.0141 (16)	0.0020 (15)
C132	0.089 (4)	0.038 (3)	0.032 (2)	0.012 (3)	0.010 (2)	−0.0023 (18)
C133	0.079 (4)	0.048 (3)	0.040 (2)	0.022 (3)	0.009 (2)	0.015 (2)
C134	0.049 (3)	0.069 (3)	0.033 (2)	0.010 (3)	0.005 (2)	0.017 (2)
C135	0.050 (3)	0.059 (3)	0.038 (2)	0.000 (3)	−0.002 (2)	0.000 (2)
C136	0.044 (3)	0.039 (2)	0.040 (2)	0.004 (2)	0.0051 (19)	0.0015 (18)
C141	0.048 (3)	0.047 (2)	0.0304 (18)	−0.003 (2)	0.0123 (18)	−0.0095 (19)
C142	0.062 (3)	0.086 (4)	0.031 (2)	−0.011 (3)	0.017 (2)	0.007 (2)
C143	0.066 (4)	0.114 (5)	0.057 (3)	−0.019 (4)	0.036 (3)	−0.004 (3)
C144	0.048 (3)	0.102 (5)	0.077 (4)	−0.009 (3)	0.027 (3)	−0.025 (3)
C145	0.051 (3)	0.074 (4)	0.059 (3)	0.005 (3)	0.015 (2)	−0.009 (3)
C146	0.053 (3)	0.049 (3)	0.042 (2)	0.001 (2)	0.013 (2)	−0.009 (2)
C231	0.036 (2)	0.038 (2)	0.0216 (17)	0.0006 (19)	0.0056 (15)	−0.0025 (15)
C232	0.051 (3)	0.044 (3)	0.030 (2)	0.009 (2)	0.0091 (19)	0.0015 (17)
C233	0.054 (3)	0.058 (3)	0.0256 (19)	−0.005 (2)	0.0120 (19)	0.0041 (18)
C234	0.048 (3)	0.055 (3)	0.035 (2)	−0.004 (2)	0.0181 (19)	−0.017 (2)
C235	0.048 (3)	0.044 (3)	0.040 (2)	0.007 (2)	0.0115 (19)	−0.0124 (19)
C236	0.052 (3)	0.035 (2)	0.0275 (18)	0.004 (2)	0.0074 (17)	0.0002 (16)
C241	0.038 (2)	0.037 (2)	0.0230 (17)	−0.0039 (19)	0.0057 (16)	0.0029 (15)
C242	0.043 (3)	0.047 (3)	0.0343 (19)	0.004 (2)	0.0088 (17)	0.0027 (18)
C243	0.040 (3)	0.078 (4)	0.049 (2)	0.009 (3)	0.007 (2)	0.000 (2)
C244	0.036 (3)	0.078 (4)	0.067 (3)	0.000 (3)	−0.004 (2)	0.015 (3)
C245	0.057 (3)	0.056 (3)	0.040 (2)	−0.013 (3)	−0.009 (2)	0.007 (2)
C246	0.049 (3)	0.040 (2)	0.0302 (19)	−0.001 (2)	0.0042 (18)	0.0046 (17)

Geometric parameters (Å, º)

Cu1—N1	2.055 (3)	C135—C136	1.377 (6)
Cu1—N2	2.065 (3)	C135—H135	0.9500
Cu1—I1	2.6182 (6)	C136—H136	0.9500
Cu1—I1^i	2.7264 (6)	C141—C146	1.396 (6)
I1—Cu1^i	2.7264 (6)	C141—C142	1.407 (5)
N1—C11	1.286 (4)	C142—C143	1.376 (7)
N1—C1	1.472 (5)	C142—H142	0.9500
N2—C21	1.281 (4)	C143—C144	1.382 (8)
N2—C2	1.483 (5)	C143—H143	0.9500
C1—C3	1.522 (5)	C144—C145	1.370 (7)
C1—H1A	0.9900	C144—H144	0.9500
C1—H1B	0.9900	C145—C146	1.367 (6)
C2—C3	1.515 (5)	C145—H145	0.9500
C2—H2A	0.9900	C146—H146	0.9500
C2—H2B	0.9900	C231—C236	1.383 (5)
C3—H3A	0.9900	C231—C232	1.391 (5)
C3—H3B	0.9900	C232—C233	1.385 (6)
C11—C12	1.429 (6)	C232—H232	0.9500
C11—H11	0.9500	C233—C234	1.363 (6)
C12—C13	1.350 (5)	C233—H233	0.9500
C12—H12	0.9500	C234—C235	1.366 (6)
C13—C141	1.479 (6)	C234—H234	0.9500
C13—C131	1.488 (6)	C235—C236	1.386 (5)
C21—C22	1.427 (6)	C235—H235	0.9500
C21—H21	0.9500	C236—H236	0.9500
C22—C23	1.348 (5)	C241—C242	1.399 (5)
C22—H22	0.9500	C241—C246	1.403 (5)
C23—C241	1.475 (5)	C242—C243	1.371 (6)
C23—C231	1.496 (5)	C242—H242	0.9500
C131—C132	1.387 (6)	C243—C244	1.376 (7)
C131—C136	1.388 (6)	C243—H243	0.9500
C132—C133	1.378 (6)	C244—C245	1.381 (7)
C132—H132	0.9500	C244—H244	0.9500
C133—C134	1.358 (6)	C245—C246	1.371 (6)
C133—H133	0.9500	C245—H245	0.9500
C134—C135	1.378 (6)	C246—H246	0.9500
C134—H134	0.9500
N1—Cu1—N2	100.17 (12)	C136—C135—C134	119.8 (4)
N1—Cu1—I1	122.48 (9)	C136—C135—H135	120.1
N2—Cu1—I1	122.34 (9)	C134—C135—H135	120.1
N1—Cu1—I1^i	103.36 (9)	C135—C136—C131	121.4 (4)
N2—Cu1—I1^i	100.53 (9)	C135—C136—H136	119.3
I1—Cu1—I1^i	104.517 (17)	C131—C136—H136	119.3
Cu1—I1—Cu1^i	75.483 (18)	C146—C141—C142	117.0 (4)
C11—N1—C1	115.8 (3)	C146—C141—C13	122.1 (3)
C11—N1—Cu1	130.4 (3)	C142—C141—C13	120.9 (4)
C1—N1—Cu1	113.21 (19)	C143—C142—C141	120.1 (5)
C21—N2—C2	116.1 (3)	C143—C142—H142	119.9
C21—N2—Cu1	129.4 (3)	C141—C142—H142	119.9
C2—N2—Cu1	113.6 (2)	C142—C143—C144	121.7 (5)
N1—C1—C3	113.1 (3)	C142—C143—H143	119.2
N1—C1—H1A	109.0	C144—C143—H143	119.2
C3—C1—H1A	109.0	C145—C144—C143	118.3 (5)
N1—C1—H1B	109.0	C145—C144—H144	120.9
C3—C1—H1B	109.0	C143—C144—H144	120.9
H1A—C1—H1B	107.8	C146—C145—C144	121.1 (5)
N2—C2—C3	112.8 (3)	C146—C145—H145	119.4
N2—C2—H2A	109.0	C144—C145—H145	119.4
C3—C2—H2A	109.0	C145—C146—C141	121.7 (4)
N2—C2—H2B	109.0	C145—C146—H146	119.1
C3—C2—H2B	109.0	C141—C146—H146	119.1
H2A—C2—H2B	107.8	C236—C231—C232	118.6 (3)
C2—C3—C1	114.9 (4)	C236—C231—C23	121.0 (3)
C2—C3—H3A	108.5	C232—C231—C23	120.4 (3)
C1—C3—H3A	108.5	C233—C232—C231	120.0 (4)
C2—C3—H3B	108.5	C233—C232—H232	120.0
C1—C3—H3B	108.5	C231—C232—H232	120.0
H3A—C3—H3B	107.5	C234—C233—C232	120.7 (4)
N1—C11—C12	123.2 (4)	C234—C233—H233	119.7
N1—C11—H11	118.4	C232—C233—H233	119.7
C12—C11—H11	118.4	C233—C234—C235	119.9 (4)
C13—C12—C11	125.2 (4)	C233—C234—H234	120.0
C13—C12—H12	117.4	C235—C234—H234	120.0
C11—C12—H12	117.4	C234—C235—C236	120.3 (4)
C12—C13—C141	121.0 (4)	C234—C235—H235	119.8
C12—C13—C131	121.2 (4)	C236—C235—H235	119.8
C141—C13—C131	117.8 (3)	C231—C236—C235	120.4 (4)
N2—C21—C22	122.4 (3)	C231—C236—H236	119.8
N2—C21—H21	118.8	C235—C236—H236	119.8
C22—C21—H21	118.8	C242—C241—C246	117.2 (4)
C23—C22—C21	125.5 (3)	C242—C241—C23	121.6 (3)
C23—C22—H22	117.2	C246—C241—C23	121.2 (4)
C21—C22—H22	117.2	C243—C242—C241	121.1 (4)
C22—C23—C241	120.5 (3)	C243—C242—H242	119.4
C22—C23—C231	121.6 (3)	C241—C242—H242	119.4
C241—C23—C231	117.9 (3)	C242—C243—C244	120.8 (5)
C132—C131—C136	117.5 (4)	C242—C243—H243	119.6
C132—C131—C13	122.6 (4)	C244—C243—H243	119.6
C136—C131—C13	119.8 (4)	C243—C244—C245	119.1 (5)
C133—C132—C131	120.9 (4)	C243—C244—H244	120.4
C133—C132—H132	119.6	C245—C244—H244	120.4
C131—C132—H132	119.6	C246—C245—C244	120.6 (4)
C134—C133—C132	120.7 (4)	C246—C245—H245	119.7
C134—C133—H133	119.7	C244—C245—H245	119.7
C132—C133—H133	119.7	C245—C246—C241	121.1 (4)
C133—C134—C135	119.8 (4)	C245—C246—H246	119.5
C133—C134—H134	120.1	C241—C246—H246	119.5
C135—C134—H134	120.1

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C132—H132···Cg1^ii	0.95	2.93	3.877 (4)	173
C12—H12···I1	0.95	3.04	3.950 (4)	161
C22—H22···I1	0.95	2.99	3.906 (3)	163

Symmetry code: (ii) x−1/2, −y+1/2, z−1/2.