(N,N-Dimethyl­dithio­carbamato-κ²S,S′)iodo­(1,10-phenanthroline-κ²N,N′)copper(II)

In the title complex, [Cu(C₃H₆NS₂)I(C₁₂H₈N₂)], the Cu^II atom is coordinated by one iodide ion, two N atoms from a phenanthroline ligand and two S atoms from a dimethyl­dithio­carbamate ligand in a distorted square-pyramidal environment.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.035
• wR factor = 0.125
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  I1     -   Cu1     ..      25.91 su

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   S1      ..       6.26 su
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

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Computing details

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(Dimethyldithiocarbamato-κ²S,S')iodo(1,10-phenanthroline-κ²N,N')copper(II)

Crystal data

[Cu(C3H6NS2)I(C12H8N2)]	F(000) = 956
Mr = 490.85	Dx = 1.858 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4094 reflections
a = 9.0506 (5) Å	θ = 3.0–27.5°
b = 11.3701 (7) Å	µ = 3.24 mm^−1
c = 17.1085 (11) Å	T = 293 K
β = 94.490 (5)°	Prism, black
V = 1755.17 (18) Å^3	0.26 × 0.25 × 0.2 mm
Z = 4

Data collection

Rigaku Mercury CCD diffractometer	4019 independent reflections
Radiation source: Sealed Tube	3553 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −11→11
Tmin = 0.411, Tmax = 0.520	k = −14→14
13281 measured reflections	l = −22→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.1032P)^2 + 0.0145P] where P = (Fo^2 + 2Fc^2)/3
4019 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.84 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

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
Cu1	0.41302 (5)	0.28530 (4)	0.53501 (3)	0.04367 (15)
I1	0.33762 (3)	0.12027 (2)	0.657885 (14)	0.04858 (13)
S1	0.31492 (11)	0.18486 (9)	0.42552 (6)	0.0502 (2)
S2	0.19532 (12)	0.38347 (8)	0.50198 (6)	0.0482 (2)
N1	0.0405 (4)	0.2651 (3)	0.38789 (18)	0.0483 (7)
N2	0.6239 (3)	0.2257 (3)	0.53924 (19)	0.0427 (6)
N3	0.5088 (4)	0.4073 (3)	0.6097 (2)	0.0491 (7)
C1	0.1664 (4)	0.2767 (3)	0.4316 (2)	0.0415 (7)
C2	0.0158 (5)	0.1696 (5)	0.3307 (2)	0.0649 (12)
H2A	0.1040	0.1227	0.3302	0.097*
H2B	−0.0079	0.2023	0.2795	0.097*
H2C	−0.0648	0.1213	0.3450	0.097*
C3	−0.0831 (5)	0.3457 (4)	0.3949 (3)	0.0562 (10)
H3A	−0.0553	0.4045	0.4336	0.084*
H3B	−0.1672	0.3027	0.4106	0.084*
H3C	−0.1082	0.3828	0.3453	0.084*
C4	0.6773 (5)	0.1321 (3)	0.5044 (3)	0.0486 (9)
H4A	0.6145	0.0883	0.4700	0.058*
C5	0.8257 (5)	0.0976 (4)	0.5180 (3)	0.0538 (10)
H5A	0.8603	0.0328	0.4917	0.065*
C6	0.9203 (4)	0.1584 (4)	0.5697 (2)	0.0515 (9)
H6A	1.0185	0.1350	0.5793	0.062*
C7	0.8656 (4)	0.2574 (3)	0.6081 (2)	0.0439 (8)
C8	0.9529 (5)	0.3261 (4)	0.6636 (2)	0.0555 (10)
H8A	1.0519	0.3066	0.6755	0.067*
C9	0.8938 (5)	0.4203 (4)	0.6999 (2)	0.0593 (11)
H9A	0.9528	0.4639	0.7362	0.071*
C10	0.7427 (5)	0.4520 (3)	0.6825 (2)	0.0484 (9)
C11	0.6734 (7)	0.5485 (4)	0.7168 (3)	0.0647 (12)
H11A	0.7276	0.5970	0.7522	0.078*
C12	0.5287 (7)	0.5700 (4)	0.6981 (3)	0.0721 (13)
H12A	0.4827	0.6328	0.7212	0.087*
C13	0.4474 (6)	0.4982 (4)	0.6441 (3)	0.0638 (11)
H13A	0.3475	0.5144	0.6319	0.077*
C14	0.6540 (4)	0.3854 (3)	0.6285 (2)	0.0403 (8)
C15	0.7166 (4)	0.2869 (3)	0.59064 (19)	0.0384 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0377 (2)	0.0420 (3)	0.0510 (3)	0.00387 (17)	0.00179 (18)	−0.00931 (18)
I1	0.04794 (18)	0.0543 (2)	0.04192 (18)	0.00217 (9)	−0.00628 (11)	0.00296 (9)
S1	0.0510 (5)	0.0491 (5)	0.0496 (5)	0.0138 (4)	−0.0012 (4)	−0.0095 (4)
S2	0.0508 (5)	0.0449 (5)	0.0484 (5)	0.0122 (4)	0.0000 (4)	−0.0084 (4)
N1	0.0506 (18)	0.0538 (18)	0.0395 (16)	0.0105 (14)	−0.0032 (13)	−0.0018 (13)
N2	0.0357 (14)	0.0411 (15)	0.0519 (17)	−0.0017 (11)	0.0073 (12)	−0.0080 (13)
N3	0.0515 (19)	0.0387 (14)	0.0579 (19)	−0.0006 (13)	0.0093 (15)	−0.0116 (14)
C1	0.050 (2)	0.0409 (17)	0.0341 (16)	0.0057 (14)	0.0065 (14)	0.0056 (13)
C2	0.074 (3)	0.065 (3)	0.052 (2)	0.016 (2)	−0.013 (2)	−0.010 (2)
C3	0.053 (2)	0.062 (2)	0.052 (2)	0.0183 (19)	−0.0016 (18)	−0.001 (2)
C4	0.042 (2)	0.0427 (19)	0.061 (2)	−0.0011 (15)	0.0039 (17)	−0.0138 (16)
C5	0.046 (2)	0.048 (2)	0.069 (3)	0.0043 (17)	0.0120 (19)	−0.0107 (19)
C6	0.0368 (19)	0.056 (2)	0.062 (2)	0.0041 (16)	0.0045 (16)	0.005 (2)
C7	0.0400 (18)	0.050 (2)	0.0422 (17)	−0.0105 (15)	0.0044 (14)	0.0038 (16)
C8	0.048 (2)	0.070 (3)	0.047 (2)	−0.015 (2)	−0.0027 (16)	0.008 (2)
C9	0.063 (3)	0.072 (3)	0.043 (2)	−0.029 (2)	0.0019 (18)	−0.003 (2)
C10	0.061 (2)	0.048 (2)	0.0373 (17)	−0.0181 (17)	0.0094 (15)	−0.0027 (15)
C11	0.097 (4)	0.044 (2)	0.054 (2)	−0.017 (2)	0.013 (2)	−0.0134 (19)
C12	0.091 (4)	0.048 (2)	0.078 (3)	0.005 (2)	0.010 (3)	−0.024 (2)
C13	0.070 (3)	0.053 (2)	0.069 (3)	0.010 (2)	0.002 (2)	−0.020 (2)
C14	0.0458 (19)	0.0355 (17)	0.0408 (18)	−0.0064 (13)	0.0104 (14)	−0.0006 (13)
C15	0.0381 (17)	0.0400 (17)	0.0374 (16)	−0.0073 (13)	0.0050 (13)	0.0005 (13)

Geometric parameters (Å, º)

Cu1—N2	2.021 (3)	C4—C5	1.401 (6)
Cu1—N3	2.034 (3)	C4—H4A	0.9300
Cu1—S2	2.2963 (11)	C5—C6	1.369 (6)
Cu1—S1	2.3111 (11)	C5—H5A	0.9300
Cu1—I1	2.9378 (5)	C6—C7	1.412 (6)
S1—C1	1.712 (4)	C6—H6A	0.9300
S2—C1	1.715 (4)	C7—C15	1.399 (5)
N1—C1	1.319 (5)	C7—C8	1.421 (5)
N1—C3	1.459 (5)	C8—C9	1.367 (7)
N1—C2	1.467 (6)	C8—H8A	0.9300
N2—C4	1.329 (5)	C9—C10	1.423 (6)
N2—C15	1.359 (4)	C9—H9A	0.9300
N3—C13	1.332 (5)	C10—C14	1.398 (5)
N3—C14	1.352 (5)	C10—C11	1.414 (6)
C2—H2A	0.9600	C11—C12	1.346 (8)
C2—H2B	0.9600	C11—H11A	0.9300
C2—H2C	0.9600	C12—C13	1.398 (7)
C3—H3A	0.9600	C12—H12A	0.9300
C3—H3B	0.9600	C13—H13A	0.9300
C3—H3C	0.9600	C14—C15	1.433 (5)
N2—Cu1—N3	81.47 (13)	N2—C4—C5	121.9 (4)
N2—Cu1—S2	164.03 (10)	N2—C4—H4A	119.1
N3—Cu1—S2	97.95 (10)	C5—C4—H4A	119.1
N2—Cu1—S1	99.50 (9)	C6—C5—C4	120.5 (4)
N3—Cu1—S1	164.63 (11)	C6—C5—H5A	119.7
S2—Cu1—S1	76.87 (4)	C4—C5—H5A	119.7
N2—Cu1—I1	91.81 (9)	C5—C6—C7	118.7 (4)
N3—Cu1—I1	95.60 (10)	C5—C6—H6A	120.7
S2—Cu1—I1	104.10 (3)	C7—C6—H6A	120.7
S1—Cu1—I1	99.69 (3)	C15—C7—C6	117.3 (3)
C1—S1—Cu1	84.44 (13)	C15—C7—C8	119.1 (4)
C1—S2—Cu1	84.82 (13)	C6—C7—C8	123.6 (4)
C1—N1—C3	121.6 (3)	C9—C8—C7	121.2 (4)
C1—N1—C2	122.1 (3)	C9—C8—H8A	119.4
C3—N1—C2	116.3 (3)	C7—C8—H8A	119.4
C4—N2—C15	118.2 (3)	C8—C9—C10	120.5 (4)
C4—N2—Cu1	128.9 (3)	C8—C9—H9A	119.8
C15—N2—Cu1	112.6 (2)	C10—C9—H9A	119.8
C13—N3—C14	118.0 (4)	C14—C10—C11	116.4 (4)
C13—N3—Cu1	129.4 (3)	C14—C10—C9	119.5 (4)
C14—N3—Cu1	112.5 (2)	C11—C10—C9	124.1 (4)
N1—C1—S1	123.5 (3)	C12—C11—C10	119.8 (4)
N1—C1—S2	123.1 (3)	C12—C11—H11A	120.1
S1—C1—S2	113.4 (2)	C10—C11—H11A	120.1
N1—C2—H2A	109.5	C11—C12—C13	120.2 (4)
N1—C2—H2B	109.5	C11—C12—H12A	119.9
H2A—C2—H2B	109.5	C13—C12—H12A	119.9
N1—C2—H2C	109.5	N3—C13—C12	121.9 (5)
H2A—C2—H2C	109.5	N3—C13—H13A	119.0
H2B—C2—H2C	109.5	C12—C13—H13A	119.0
N1—C3—H3A	109.5	N3—C14—C10	123.7 (3)
N1—C3—H3B	109.5	N3—C14—C15	116.6 (3)
H3A—C3—H3B	109.5	C10—C14—C15	119.7 (4)
N1—C3—H3C	109.5	N2—C15—C7	123.5 (3)
H3A—C3—H3C	109.5	N2—C15—C14	116.6 (3)
H3B—C3—H3C	109.5	C7—C15—C14	119.9 (3)