[5-Bromo-N-(2-pyridyl­ethyl­sulfanyl­ethyl)salicyl­idene­iminato-κ⁴N,N′,O,S]copper(II) perchlorate

The Cu atom in the title compound, [Cu(C₁₆H₁₆BrN₂OS)]ClO₄, exists in a distorted square-planar geometry. The compound exists as discrete ions.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.70

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.145     0.576
            Tmin' and Tmax expected:      0.175     0.576
            RR' =      0.827
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for        Cl1
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1     ..  C13     ..       3.19 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

[5-Bromo-N-(2-pyridylethylsulfanylethyl)salicylideneiminato- κ⁴N,N',O,S]copper(II) perchlorate

Crystal data

[Cu(C16H16BrN2OS)]ClO4	F(000) = 1052
Mr = 527.27	Dx = 1.917 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5071 reflections
a = 9.9542 (6) Å	θ = 2.5–26.4°
b = 8.8479 (6) Å	µ = 3.68 mm^−1
c = 21.223 (1) Å	T = 113 K
β = 102.263 (1)°	Plate, blue
V = 1826.5 (2) Å^3	0.45 × 0.43 × 0.15 mm
Z = 4

Data collection

Siemens P4 CCD area-detector diffractometer	3657 independent reflections
Radiation source: medium-focus sealed tube	2645 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.145, Tmax = 0.576	k = −11→11
9902 measured reflections	l = −23→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0558P)^2] where P = (Fo^2 + 2Fc^2)/3
3657 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 1.72 e Å^−3
0 restraints	Δρmin = −1.49 e Å^−3

Special details

Experimental. A value of µ*2r of 1.40 was used during the data reduction.

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

	x	y	z	Uiso*/Ueq
Br1	1.08500 (5)	0.36859 (5)	0.63028 (2)	0.0279 (2)
Cu1	0.42616 (6)	0.76314 (5)	0.56498 (2)	0.0158 (2)
S1	0.2332 (1)	0.7828 (1)	0.61047 (5)	0.0192 (2)
Cl1	1.0114 (1)	0.8183 (1)	0.78729 (5)	0.0229 (3)
O1	0.5502 (3)	0.6743 (3)	0.5214 (1)	0.019 (1)
O2	1.0530 (5)	0.6669 (3)	0.7809 (2)	0.063 (2)
O3	0.8659 (4)	0.8309 (4)	0.7706 (2)	0.048 (1)
O4	1.0685 (4)	0.9126 (4)	0.7449 (2)	0.039 (1)
O5	1.0603 (4)	0.8677 (3)	0.8524 (1)	0.040 (1)
N1	0.5311 (4)	0.7268 (3)	0.6496 (2)	0.018 (1)
N2	0.3370 (4)	0.8818 (3)	0.4893 (2)	0.016 (1)
C1	0.6616 (5)	0.6016 (4)	0.5484 (2)	0.014 (1)
C2	0.7373 (5)	0.5297 (4)	0.5074 (2)	0.017 (1)
C3	0.8583 (5)	0.4593 (4)	0.5314 (2)	0.018 (1)
C4	0.9124 (5)	0.4577 (4)	0.5976 (2)	0.016 (1)
C5	0.8403 (5)	0.5226 (4)	0.6390 (2)	0.017 (1)
C6	0.7149 (5)	0.5932 (4)	0.6150 (2)	0.014 (1)
C7	0.6451 (5)	0.6562 (4)	0.6621 (2)	0.018 (1)
C8	0.4716 (5)	0.7855 (5)	0.7027 (2)	0.022 (1)
C9	0.3234 (5)	0.7412 (5)	0.6915 (2)	0.026 (1)
C10	0.2092 (5)	0.9869 (4)	0.6091 (2)	0.023 (1)
C11	0.2928 (5)	1.0659 (4)	0.5671 (2)	0.020 (1)
C12	0.2693 (5)	1.0085 (4)	0.4990 (2)	0.018 (1)
C13	0.1853 (5)	1.0807 (4)	0.4483 (2)	0.024 (1)
C14	0.1752 (6)	1.0268 (5)	0.3863 (2)	0.031 (1)
C15	0.2485 (5)	0.9010 (5)	0.3769 (2)	0.028 (1)
C16	0.3267 (5)	0.8301 (4)	0.4293 (2)	0.023 (1)
H2	0.7024	0.5308	0.4621	0.021*
H3	0.9066	0.4109	0.5029	0.021*
H5	0.8762	0.5194	0.6842	0.021*
H7	0.6881	0.6439	0.7062	0.021*
H8a	0.4800	0.8970	0.7047	0.027*
H8b	0.5220	0.7435	0.7443	0.027*
H9a	0.2791	0.7959	0.7223	0.032*
H9b	0.3167	0.6316	0.6997	0.032*
H10a	0.1106	1.0100	0.5928	0.028*
H10b	0.2361	1.0265	0.6536	0.028*
H11a	0.2709	1.1751	0.5660	0.024*
H11b	0.3916	1.0547	0.5872	0.024*
H13	0.1344	1.1673	0.4558	0.029*
H14	0.1182	1.0764	0.3507	0.037*
H15	0.2450	0.8635	0.3347	0.033*
H16	0.3756	0.7412	0.4228	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0269 (3)	0.0348 (2)	0.0216 (2)	0.0148 (2)	0.0047 (2)	0.0037 (2)
Cu1	0.0209 (4)	0.0167 (2)	0.0095 (2)	0.0049 (2)	0.0027 (2)	−0.00014 (17)
S1	0.0247 (7)	0.0169 (4)	0.0167 (5)	0.0002 (4)	0.0060 (4)	−0.0019 (4)
Cl1	0.0334 (8)	0.0180 (4)	0.0151 (5)	−0.0016 (4)	0.0002 (5)	0.0007 (3)
O1	0.023 (2)	0.023 (1)	0.011 (1)	0.008 (1)	0.002 (1)	0.000 (1)
O2	0.120 (5)	0.020 (2)	0.041 (2)	0.016 (2)	−0.005 (2)	−0.002 (2)
O3	0.029 (3)	0.076 (2)	0.036 (2)	−0.009 (2)	0.000 (2)	−0.001 (2)
O4	0.049 (3)	0.041 (2)	0.029 (2)	−0.006 (2)	0.014 (2)	0.010 (2)
O5	0.061 (3)	0.039 (2)	0.014 (2)	0.001 (2)	−0.007 (2)	−0.004 (1)
N1	0.028 (3)	0.017 (2)	0.008 (2)	0.005 (2)	0.005 (2)	−0.001 (1)
N2	0.019 (2)	0.016 (2)	0.013 (2)	−0.001 (1)	0.004 (2)	0.001 (1)
C1	0.016 (3)	0.011 (2)	0.016 (2)	−0.002 (2)	0.002 (2)	−0.002 (1)
C2	0.024 (3)	0.018 (2)	0.010 (2)	−0.003 (2)	0.003 (2)	−0.001 (1)
C3	0.025 (3)	0.013 (2)	0.016 (2)	0.000 (2)	0.008 (2)	−0.004 (1)
C4	0.016 (3)	0.012 (2)	0.018 (2)	0.003 (2)	0.001 (2)	0.002 (1)
C5	0.024 (3)	0.018 (2)	0.009 (2)	−0.001 (2)	0.002 (2)	−0.001 (1)
C6	0.021 (3)	0.012 (2)	0.012 (2)	0.002 (2)	0.006 (2)	−0.002 (1)
C7	0.027 (3)	0.014 (2)	0.011 (2)	0.001 (2)	0.002 (2)	0.000 (1)
C8	0.030 (3)	0.028 (2)	0.009 (2)	0.014 (2)	0.004 (2)	−0.004 (2)
C9	0.037 (4)	0.029 (2)	0.015 (2)	0.011 (2)	0.011 (2)	0.003 (2)
C10	0.028 (3)	0.019 (2)	0.023 (2)	0.007 (2)	0.007 (2)	−0.003 (2)
C11	0.025 (3)	0.015 (2)	0.019 (2)	0.000 (2)	0.001 (2)	−0.001 (2)
C12	0.022 (3)	0.013 (2)	0.019 (2)	−0.003 (2)	0.004 (2)	0.000 (2)
C13	0.027 (3)	0.016 (2)	0.028 (2)	0.001 (2)	0.003 (2)	0.006 (2)
C14	0.037 (4)	0.031 (2)	0.020 (2)	−0.003 (2)	−0.004 (2)	0.011 (2)
C15	0.038 (3)	0.032 (2)	0.011 (2)	−0.009 (2)	0.001 (2)	0.002 (2)
C16	0.033 (3)	0.020 (2)	0.017 (2)	−0.003 (2)	0.006 (2)	−0.001 (2)

Geometric parameters (Å, º)

Br1—C4	1.884 (4)	C8—C9	1.496 (7)
Cu1—N1	1.904 (3)	C10—C11	1.514 (6)
Cu1—N2	1.966 (3)	C11—C12	1.501 (5)
Cu1—O1	1.866 (3)	C12—C13	1.372 (6)
Cu1—S1	2.332 (1)	C13—C14	1.384 (6)
S1—C9	1.801 (4)	C14—C15	1.368 (7)
S1—C10	1.821 (4)	C15—C16	1.366 (6)
Cl1—O2	1.418 (3)	C2—H2	0.95
Cl1—O3	1.420 (4)	C3—H3	0.95
Cl1—O5	1.432 (3)	C5—H5	0.95
Cl1—O4	1.431 (3)	C7—H7	0.95
O1—C1	1.305 (5)	C8—H8a	0.99
N1—C7	1.272 (6)	C8—H8b	0.99
N1—C8	1.474 (5)	C9—H9a	0.99
N2—C16	1.337 (5)	C9—H9b	0.99
N2—C12	1.346 (5)	C10—H10a	0.99
C1—C6	1.403 (5)	C10—H10b	0.99
C1—C2	1.415 (5)	C11—H11a	0.99
C2—C3	1.356 (6)	C11—H11b	0.99
C3—C4	1.394 (5)	C13—H13	0.95
C4—C5	1.372 (5)	C14—H14	0.95
C5—C6	1.392 (6)	C15—H15	0.95
C6—C7	1.445 (5)	C16—H16	0.95
N1—Cu1—O1	96.2 (1)	C13—C12—C11	122.7 (4)
N1—Cu1—N2	157.4 (1)	C12—C13—C14	119.6 (4)
N1—Cu1—S1	87.5 (1)	C15—C14—C13	119.0 (4)
N2—Cu1—O1	92.9 (1)	C16—C15—C14	119.0 (4)
N2—Cu1—S1	91.7 (1)	N2—C16—C15	122.2 (4)
O1—Cu1—S1	157.9 (1)	C3—C2—H2	119.3
C9—S1—C10	104.8 (2)	C1—C2—H2	119.3
C9—S1—Cu1	95.3 (2)	C2—C3—H3	119.8
C10—S1—Cu1	100.6 (2)	C4—C3—H3	119.8
O2—Cl1—O3	110.7 (3)	C4—C5—H5	119.9
O2—Cl1—O5	109.6 (2)	C6—C5—H5	119.9
O3—Cl1—O5	109.7 (2)	N1—C7—H7	117.1
O2—Cl1—O4	109.1 (2)	C6—C7—H7	117.1
O3—Cl1—O4	108.5 (2)	N1—C8—H8a	109.8
O5—Cl1—O4	109.3 (2)	C9—C8—H8a	109.8
C1—O1—Cu1	125.5 (2)	N1—C8—H8b	109.8
C7—N1—C8	120.0 (3)	C9—C8—H8b	109.8
C7—N1—Cu1	124.4 (3)	H8a—C8—H8b	108.3
C8—N1—Cu1	115.6 (3)	C8—C9—H9a	109.2
C16—N2—C12	119.4 (4)	S1—C9—H9a	109.2
C16—N2—Cu1	121.7 (3)	C8—C9—H9b	109.2
C12—N2—Cu1	118.3 (3)	S1—C9—H9b	109.2
O1—C1—C6	124.9 (3)	H9a—C9—H9b	107.9
O1—C1—C2	117.8 (3)	C11—C10—H10a	109.1
C6—C1—C2	117.3 (4)	S1—C10—H10a	109.1
C3—C2—C1	121.5 (4)	C11—C10—H10b	109.1
C2—C3—C4	120.3 (4)	S1—C10—H10b	109.1
C5—C4—C3	119.9 (4)	H10a—C10—H10b	107.9
C5—C4—Br1	120.0 (3)	C12—C11—H11a	108.6
C3—C4—Br1	120.1 (3)	C10—C11—H11a	108.6
C4—C5—C6	120.3 (4)	C12—C11—H11b	108.6
C5—C6—C1	120.7 (3)	C10—C11—H11b	108.6
C5—C6—C7	116.5 (3)	H11a—C11—H11b	107.6
C1—C6—C7	122.8 (4)	C12—C13—H13	120.2
N1—C7—C6	125.8 (4)	C14—C13—H13	120.2
N1—C8—C9	109.2 (3)	C15—C14—H14	120.5
C8—C9—S1	111.9 (3)	C13—C14—H14	120.5
C11—C10—S1	112.4 (3)	C16—C15—H15	120.5
C12—C11—C10	114.7 (3)	C14—C15—H15	120.5
N2—C12—C13	120.6 (4)	N2—C16—H16	118.9
N2—C12—C11	116.6 (4)	C15—C16—H16	118.9
O1—Cu1—S1—C9	98.2 (3)	C4—C5—C6—C7	179.0 (3)
N1—Cu1—S1—C9	−2.3 (2)	O1—C1—C6—C5	−175.0 (4)
N2—Cu1—S1—C9	−159.8 (2)	C2—C1—C6—C5	2.9 (5)
O1—Cu1—S1—C10	−155.7 (3)	O1—C1—C6—C7	4.8 (6)
N1—Cu1—S1—C10	103.8 (2)	C2—C1—C6—C7	−177.4 (3)
N2—Cu1—S1—C10	−53.6 (2)	C8—N1—C7—C6	−179.9 (4)
N1—Cu1—O1—C1	5.9 (3)	Cu1—N1—C7—C6	0.6 (6)
N2—Cu1—O1—C1	165.2 (3)	C5—C6—C7—N1	178.8 (4)
S1—Cu1—O1—C1	−92.9 (4)	C1—C6—C7—N1	−0.9 (6)
O1—Cu1—N1—C7	−2.4 (4)	C7—N1—C8—C9	−131.9 (4)
N2—Cu1—N1—C7	−115.8 (4)	Cu1—N1—C8—C9	47.7 (4)
S1—Cu1—N1—C7	155.7 (3)	N1—C8—C9—S1	−48.5 (4)
O1—Cu1—N1—C8	178.0 (3)	C10—S1—C9—C8	−75.1 (3)
N2—Cu1—N1—C8	64.7 (5)	Cu1—S1—C9—C8	27.4 (3)
S1—Cu1—N1—C8	−23.8 (3)	C9—S1—C10—C11	112.0 (3)
O1—Cu1—N2—C16	32.2 (4)	Cu1—S1—C10—C11	13.5 (3)
N1—Cu1—N2—C16	146.1 (4)	S1—C10—C11—C12	54.7 (5)
S1—Cu1—N2—C16	−126.2 (3)	C16—N2—C12—C13	3.0 (6)
O1—Cu1—N2—C12	−156.6 (3)	Cu1—N2—C12—C13	−168.4 (3)
N1—Cu1—N2—C12	−42.7 (6)	C16—N2—C12—C11	−176.0 (4)
S1—Cu1—N2—C12	45.0 (3)	Cu1—N2—C12—C11	12.6 (5)
Cu1—O1—C1—C6	−7.8 (5)	C10—C11—C12—N2	−81.1 (5)
Cu1—O1—C1—C2	174.4 (3)	C10—C11—C12—C13	99.9 (5)
O1—C1—C2—C3	176.1 (4)	N2—C12—C13—C14	−3.1 (7)
C6—C1—C2—C3	−1.9 (5)	C11—C12—C13—C14	175.9 (4)
C1—C2—C3—C4	−0.7 (6)	C12—C13—C14—C15	0.7 (7)
C2—C3—C4—C5	2.5 (6)	C13—C14—C15—C16	1.6 (7)
C2—C3—C4—Br1	−176.8 (3)	C12—N2—C16—C15	−0.6 (7)
C3—C4—C5—C6	−1.4 (6)	Cu1—N2—C16—C15	170.5 (4)
Br1—C4—C5—C6	177.8 (3)	C14—C15—C16—N2	−1.7 (7)
C4—C5—C6—C1	−1.3 (6)