Bis(trans-(E)-2-{[4-(4-acetyl­phenyl­sulfanyl)­phenyl­imino-κN]­methyl}phenolato-κO)copper(II)

Hebbachi, R.; Benali-Cherif, N.

doi:10.1107/S1600536805015539

Bis(trans-(E)-2-{[4-(4-acetylphenylsulfanyl)phenylimino-κN]methyl}phenolato-κO)copper(II)

In the structure of the mononuclear title complex, [Cu(C₂₁H₁₆NO₂S)₂], the Cu^II atom, which lies on an inversion centre, displays approximately square-planar coordination geometry. The bidentate ligands coordinate through their phenolate O and imine N atoms in a mutually trans orientation. The structure is stabilized by a three-dimensional network of C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015539/sj6083sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015539/sj6083Isup2.hkl Contains datablock I

CCDC reference: 274635

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.034
wR factor = 0.119
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C21
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O2      ..       2.73 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         46
            C1  -O1  -CU  -O1    120.00 10.00   1.555   1.555   1.555   2.565
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         53
            C7  -N   -CU  -N      -4.00100.00   1.555   1.555   1.555   2.565
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         54
            C8  -N   -CU  -N     167.00 10.00   1.555   1.555   1.555   2.565

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

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

Computing details top

Data collection: KappaCCD (Nonius, 1998); cell refinement: DENZO and SCAKEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCAKEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top

Crystal data top

[Cu(C₂₁H₁₆NO₂S)₂]	Z = 1
M_r = 756.40	F(000) = 391
Triclinic, P1	D_x = 1.422 Mg m⁻³
Hall symbol: -P 1	Melting point: 233 K
a = 9.172 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.032 (3) Å	Cell parameters from 6926 reflections
c = 11.106 (3) Å	θ = 2.2–26.0°
α = 60.825 (2)°	µ = 0.78 mm⁻¹
β = 67.219 (2)°	T = 293 K
γ = 89.136 (3)°	Prism, brown
V = 883.4 (4) Å³	0.3 × 0.1 × 0.1 mm

Data collection top

KappaCCD diffractometer	2921 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
φ scans	h = −11→11
6940 measured reflections	k = −13→13
3396 independent reflections	l = −11→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.063P)² + 0.2786P] where P = (F_o² + 2F_c²)/3
3396 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2523 (3)	0.7027 (3)	−0.0563 (3)	0.0330 (5)
C2	0.4191 (3)	0.7658 (3)	−0.1306 (3)	0.0438 (6)
H2	0.4939	0.7292	−0.1814	0.053*
C3	0.4719 (3)	0.8803 (3)	−0.1286 (4)	0.0487 (7)
H3	0.5822	0.9200	−0.1780	0.058*
C4	0.3640 (4)	0.9382 (3)	−0.0541 (4)	0.0509 (7)
H4	0.4009	1.0174	−0.0559	0.061*
C5	0.2022 (4)	0.8765 (3)	0.0220 (3)	0.0432 (6)
H5	0.1296	0.9133	0.0741	0.052*
C6	0.1435 (3)	0.7588 (3)	0.0230 (3)	0.0321 (5)
C8	−0.2767 (3)	0.5593 (2)	0.2080 (3)	0.0284 (5)
C9	−0.3695 (3)	0.6583 (3)	0.1660 (3)	0.0368 (6)
H9	−0.3201	0.7493	0.0807	0.044*
C10	−0.5363 (3)	0.6216 (3)	0.2512 (3)	0.0402 (6)
H10	−0.5988	0.6877	0.2221	0.048*
C11	−0.6098 (3)	0.4869 (3)	0.3793 (3)	0.0339 (5)
C12	−0.5161 (3)	0.3890 (3)	0.4232 (3)	0.0365 (5)
H12	−0.5651	0.2993	0.5109	0.044*
C13	−0.3506 (3)	0.4245 (3)	0.3371 (3)	0.0347 (5)
H13	−0.2885	0.3579	0.3656	0.042*
C14	−0.8882 (3)	0.3438 (3)	0.4245 (3)	0.0332 (5)
C15	−0.7987 (3)	0.3604 (3)	0.2821 (3)	0.0384 (6)
H15	−0.7021	0.4282	0.2142	0.046*
C16	−0.8525 (3)	0.2767 (3)	0.2411 (3)	0.0392 (6)
H16	−0.7895	0.2862	0.1470	0.047*
C17	−1.0000 (3)	0.1778 (3)	0.3384 (3)	0.0363 (6)
C18	−1.0922 (3)	0.1675 (3)	0.4780 (3)	0.0398 (6)
H18	−1.1928	0.1052	0.5429	0.048*
C19	−1.0369 (3)	0.2478 (3)	0.5212 (3)	0.0389 (6)
H19	−1.0993	0.2379	0.6156	0.047*
C20	−1.0472 (4)	0.0853 (3)	0.2911 (3)	0.0441 (7)
C21	−1.2184 (4)	0.0012 (4)	0.3761 (4)	0.0635 (9)
H21A	−1.2302	−0.0528	0.3326	0.095*
H21B	−1.2914	0.0649	0.3679	0.095*
H21C	−1.2429	−0.0624	0.4820	0.095*
N	−0.1044 (2)	0.5949 (2)	0.1184 (2)	0.0297 (4)
O1	0.2079 (2)	0.5977 (2)	−0.0664 (2)	0.0431 (5)
O2	−0.9483 (3)	0.0770 (2)	0.1857 (3)	0.0601 (6)
S	−0.82363 (8)	0.44069 (8)	0.48992 (8)	0.0442 (2)
Cu	0.0000	0.5000	0.0000	0.02865 (15)
C7	−0.0272 (3)	0.7014 (3)	0.1053 (3)	0.0320 (5)
H7	−0.0894	0.7450	0.1547	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0291 (12)	0.0352 (12)	0.0372 (13)	0.0031 (10)	−0.0142 (11)	−0.0207 (11)
C2	0.0287 (13)	0.0511 (16)	0.0523 (16)	0.0034 (11)	−0.0111 (13)	−0.0322 (14)
C3	0.0349 (14)	0.0472 (16)	0.0602 (18)	−0.0036 (12)	−0.0210 (14)	−0.0249 (14)
C4	0.0486 (17)	0.0421 (15)	0.074 (2)	0.0015 (12)	−0.0311 (16)	−0.0348 (15)
C5	0.0451 (16)	0.0401 (14)	0.0594 (17)	0.0086 (12)	−0.0249 (15)	−0.0347 (13)
C6	0.0305 (12)	0.0336 (12)	0.0363 (12)	0.0043 (9)	−0.0147 (11)	−0.0208 (10)
C8	0.0256 (11)	0.0337 (12)	0.0301 (11)	0.0063 (9)	−0.0087 (10)	−0.0221 (10)
C9	0.0352 (13)	0.0326 (12)	0.0352 (13)	0.0095 (10)	−0.0098 (12)	−0.0167 (11)
C10	0.0330 (13)	0.0436 (14)	0.0438 (14)	0.0164 (11)	−0.0140 (12)	−0.0250 (12)
C11	0.0265 (12)	0.0450 (14)	0.0375 (13)	0.0075 (10)	−0.0102 (11)	−0.0294 (12)
C12	0.0333 (13)	0.0345 (12)	0.0355 (13)	0.0020 (10)	−0.0102 (11)	−0.0173 (11)
C13	0.0298 (12)	0.0327 (12)	0.0391 (13)	0.0089 (10)	−0.0145 (11)	−0.0174 (11)
C14	0.0270 (12)	0.0368 (13)	0.0373 (13)	0.0100 (10)	−0.0135 (11)	−0.0207 (11)
C15	0.0303 (13)	0.0432 (14)	0.0354 (13)	0.0034 (10)	−0.0083 (11)	−0.0207 (11)
C16	0.0392 (14)	0.0449 (14)	0.0331 (13)	0.0095 (11)	−0.0140 (12)	−0.0214 (11)
C17	0.0387 (14)	0.0315 (12)	0.0413 (14)	0.0112 (10)	−0.0240 (12)	−0.0158 (11)
C18	0.0303 (13)	0.0362 (13)	0.0414 (14)	0.0037 (10)	−0.0128 (12)	−0.0143 (11)
C19	0.0293 (13)	0.0435 (14)	0.0372 (13)	0.0091 (11)	−0.0088 (12)	−0.0209 (12)
C20	0.0560 (18)	0.0322 (13)	0.0471 (16)	0.0118 (12)	−0.0322 (15)	−0.0154 (12)
C21	0.071 (2)	0.0485 (18)	0.069 (2)	−0.0019 (15)	−0.0391 (19)	−0.0221 (16)
N	0.0260 (10)	0.0322 (10)	0.0318 (10)	0.0055 (8)	−0.0097 (9)	−0.0196 (8)
O1	0.0259 (9)	0.0531 (11)	0.0623 (12)	0.0044 (8)	−0.0096 (9)	−0.0456 (10)
O2	0.0807 (17)	0.0511 (13)	0.0574 (13)	0.0123 (11)	−0.0325 (14)	−0.0326 (11)
S	0.0249 (3)	0.0648 (5)	0.0502 (4)	0.0061 (3)	−0.0059 (3)	−0.0427 (4)
Cu	0.0222 (2)	0.0313 (2)	0.0364 (3)	0.00459 (15)	−0.00868 (19)	−0.02337 (19)
C7	0.0331 (13)	0.0349 (12)	0.0348 (12)	0.0080 (10)	−0.0120 (11)	−0.0249 (10)

Geometric parameters (Å, º) top

C1—O1	1.302 (3)	C14—C15	1.387 (4)
C1—C6	1.409 (4)	C14—C19	1.391 (4)
C1—C2	1.414 (3)	C14—S	1.769 (3)
C2—C3	1.374 (4)	C15—C16	1.379 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.391 (5)	C16—C17	1.396 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.371 (4)	C17—C18	1.395 (4)
C4—H4	0.9300	C17—C20	1.490 (4)
C5—C6	1.407 (3)	C18—C19	1.374 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.430 (3)	C19—H19	0.9300
C8—C9	1.385 (3)	C20—O2	1.217 (4)
C8—C13	1.388 (3)	C20—C21	1.504 (4)
C8—N	1.436 (3)	C21—H21A	0.9600
C9—C10	1.387 (4)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C10—C11	1.384 (4)	N—C7	1.297 (3)
C10—H10	0.9300	N—Cu	2.019 (2)
C11—C12	1.387 (4)	O1—Cu	1.8817 (18)
C11—S	1.780 (3)	Cu—O1ⁱ	1.8817 (18)
C12—C13	1.379 (3)	Cu—Nⁱ	2.019 (2)
C12—H12	0.9300	C7—H7	0.9300
C13—H13	0.9300

O1—C1—C6	123.8 (2)	C16—C15—C14	120.2 (2)
O1—C1—C2	118.4 (2)	C16—C15—H15	119.9
C6—C1—C2	117.8 (2)	C14—C15—H15	119.9
C3—C2—C1	120.8 (3)	C15—C16—C17	121.2 (3)
C3—C2—H2	119.6	C15—C16—H16	119.4
C1—C2—H2	119.6	C17—C16—H16	119.4
C2—C3—C4	121.4 (3)	C18—C17—C16	117.8 (2)
C2—C3—H3	119.3	C18—C17—C20	123.5 (2)
C4—C3—H3	119.3	C16—C17—C20	118.6 (3)
C5—C4—C3	118.8 (3)	C19—C18—C17	121.1 (2)
C5—C4—H4	120.6	C19—C18—H18	119.4
C3—C4—H4	120.6	C17—C18—H18	119.4
C4—C5—C6	121.4 (3)	C18—C19—C14	120.4 (3)
C4—C5—H5	119.3	C18—C19—H19	119.8
C6—C5—H5	119.3	C14—C19—H19	119.8
C5—C6—C1	119.8 (2)	O2—C20—C17	120.5 (3)
C5—C6—C7	117.6 (2)	O2—C20—C21	120.4 (3)
C1—C6—C7	122.6 (2)	C17—C20—C21	119.2 (3)
C9—C8—C13	119.8 (2)	C20—C21—H21A	109.5
C9—C8—N	120.5 (2)	C20—C21—H21B	109.5
C13—C8—N	119.7 (2)	H21A—C21—H21B	109.5
C8—C9—C10	120.0 (2)	C20—C21—H21C	109.5
C8—C9—H9	120.0	H21A—C21—H21C	109.5
C10—C9—H9	120.0	H21B—C21—H21C	109.5
C11—C10—C9	120.0 (2)	C7—N—C8	115.35 (19)
C11—C10—H10	120.0	C7—N—Cu	123.59 (16)
C9—C10—H10	120.0	C8—N—Cu	120.55 (14)
C10—C11—C12	119.9 (2)	C1—O1—Cu	130.51 (17)
C10—C11—S	120.00 (19)	C14—S—C11	102.10 (12)
C12—C11—S	120.1 (2)	O1—Cu—O1ⁱ	180.00 (15)
C13—C12—C11	120.2 (2)	O1—Cu—N	91.38 (8)
C13—C12—H12	119.9	O1ⁱ—Cu—N	88.62 (8)
C11—C12—H12	119.9	O1—Cu—Nⁱ	88.62 (8)
C12—C13—C8	120.1 (2)	O1ⁱ—Cu—Nⁱ	91.38 (8)
C12—C13—H13	119.9	N—Cu—Nⁱ	180.0
C8—C13—H13	119.9	N—C7—C6	126.9 (2)
C15—C14—C19	119.2 (2)	N—C7—H7	116.6
C15—C14—S	123.2 (2)	C6—C7—H7	116.6
C19—C14—S	117.7 (2)

O1—C1—C2—C3	177.5 (3)	C15—C14—C19—C18	1.8 (4)
C6—C1—C2—C3	−1.8 (4)	S—C14—C19—C18	−178.77 (19)
C1—C2—C3—C4	−0.1 (5)	C18—C17—C20—O2	−163.9 (3)
C2—C3—C4—C5	1.8 (5)	C16—C17—C20—O2	13.4 (4)
C3—C4—C5—C6	−1.5 (5)	C18—C17—C20—C21	15.5 (4)
C4—C5—C6—C1	−0.3 (4)	C16—C17—C20—C21	−167.1 (2)
C4—C5—C6—C7	−180.0 (3)	C9—C8—N—C7	59.5 (3)
O1—C1—C6—C5	−177.3 (2)	C13—C8—N—C7	−120.8 (3)
C2—C1—C6—C5	2.0 (4)	C9—C8—N—Cu	−112.5 (2)
O1—C1—C6—C7	2.4 (4)	C13—C8—N—Cu	67.1 (3)
C2—C1—C6—C7	−178.4 (2)	C6—C1—O1—Cu	5.6 (4)
C13—C8—C9—C10	−1.2 (4)	C2—C1—O1—Cu	−173.65 (19)
N—C8—C9—C10	178.4 (2)	C15—C14—S—C11	−24.0 (2)
C8—C9—C10—C11	0.9 (4)	C19—C14—S—C11	156.7 (2)
C9—C10—C11—C12	0.6 (4)	C10—C11—S—C14	100.3 (2)
C9—C10—C11—S	179.2 (2)	C12—C11—S—C14	−81.1 (2)
C10—C11—C12—C13	−1.8 (4)	C1—O1—Cu—O1ⁱ	120 (10)
S—C11—C12—C13	179.6 (2)	C1—O1—Cu—N	−10.3 (2)
C11—C12—C13—C8	1.4 (4)	C1—O1—Cu—Nⁱ	169.7 (2)
C9—C8—C13—C12	0.1 (4)	C7—N—Cu—O1	11.1 (2)
N—C8—C13—C12	−179.5 (2)	C8—N—Cu—O1	−177.48 (17)
C19—C14—C15—C16	−3.7 (4)	C7—N—Cu—O1ⁱ	−168.9 (2)
S—C14—C15—C16	176.9 (2)	C8—N—Cu—O1ⁱ	2.52 (17)
C14—C15—C16—C17	2.4 (4)	C7—N—Cu—Nⁱ	−4 (100)
C15—C16—C17—C18	0.7 (4)	C8—N—Cu—Nⁱ	167 (10)
C15—C16—C17—C20	−176.8 (2)	C8—N—C7—C6	−179.9 (2)
C16—C17—C18—C19	−2.6 (4)	Cu—N—C7—C6	−8.1 (4)
C20—C17—C18—C19	174.8 (2)	C5—C6—C7—N	179.2 (2)
C17—C18—C19—C14	1.3 (4)	C1—C6—C7—N	−0.4 (4)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱⁱ	0.93	2.60	3.462 (5)	154
C9—H9···O2ⁱⁱⁱ	0.93	2.73	3.550 (3)	147

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

Dihedral angles (°) between the four planes present in (I) top

Planes	P1	P2	P3	P4
P1	0	-	-	-
P2	6.21 (7)	0	-	-
P3	65.10 (6)	58.91 (8)	0	-
P4	30.13 (7)	33.78 (9)	84.12 (8)	0

Notes: P1 = Cu/O1/C1/C6/C7/N, coordination plane containing Cu atom; P2 = C1–C6, phenyl ring of the iminomethylphenolate; P3 = C8–C13, phenyl ring (4) of the diphenylsulfane; P4 = C14–C19, phenyl ring (4') of the diphenylsulfane.

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Bis(trans-(E)-2-{[4-(4-acetyl­phenyl­sulfanyl)­phenyl­imino-κN]­methyl}phenolato-κO)copper(II)

Supporting information

Key indicators

checkCIF/PLATON results

Bis(trans-(E)-2-{[4-(4-acetylphenylsulfanyl)phenylimino-κN]methyl}phenolato-κO)copper(II)