Bis­(iso­thio­cyanato-κN)­bis­[8-(methoxy­carbonyl­methoxy)­quinoline-κN]copper(II)

In the title mononuclear complex, [Cu(NSC)₂(C₁₃H₁₁NO₃)₂], the iso­thio­cyanate ions and 8-(methoxy­carbonyl­methoxy)­quinoline mol­ecules act as monodentate ligands. The ligand geometry about the Cu centre, which lies on a twofold rotation axis, can be described as square-planar or grossly distorted octahedral, formed by two N atoms of the iso­thio­cyanate ions, two quinoline N atoms and two methoxy O atoms of the 8-(methoxy­carbonyl­methoxy)­quinoline ligands. The N—Cu—N cis angles around the Cu atom vary from 88.38 (12) to 94.27 (15)° and the Cu—N bond distances are 1.950 (2) and 2.024 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.101
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.27 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.13 Ratio
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            N2  -CU1 -N2  -C13    68.00  5.00   2.655   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N1  -CU1 -N2  -C13   -94.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            N1  -CU1 -N2  -C13   176.00100.00   2.655   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         20
            O1  -CU1 -N2  -C13   -21.00  5.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         55
            CU1 -N2  -C13 -S1     72.00 19.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrystalClear (Molecular Structure Corporation, 2000; Rigaku Corporation, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); 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.

Bis(isothiocyanato-κN)bis[8-(methoxycarbonylmethoxy)quinoline-κN]copper(II)

Crystal data

[Cu(NSC)2(C13H11NO3)2]	F(000) = 1260
Mr = 614.14	Dx = 1.509 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 5205 reflections
a = 16.921 (4) Å	θ = 3.0–27.5°
b = 10.073 (2) Å	µ = 1.01 mm^−1
c = 17.590 (5) Å	T = 193 K
β = 115.647 (4)°	Block, green
V = 2702.6 (11) Å^3	0.38 × 0.24 × 0.10 mm
Z = 4

Data collection

Rigaku Mercury diffractometer	3086 independent reflections
Radiation source: fine-focus sealed tube	2849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −21→17
Absorption correction: multi-scan (Jacobson, 1998)	k = −13→13
Tmin = 0.700, Tmax = 0.906	l = −20→22
14799 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.22	w = 1/[σ^2(Fo^2) + (0.0246P)^2 + 6.2754P] where P = (Fo^2 + 2Fc^2)/3
3086 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.43 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	0.5000	0.63129 (4)	0.2500	0.02447 (14)
S1	0.33594 (6)	0.95242 (9)	0.04734 (6)	0.0485 (2)
O1	0.62229 (12)	0.60085 (18)	0.21048 (12)	0.0299 (4)
O2	0.77796 (14)	0.4745 (2)	0.31565 (15)	0.0462 (6)
O3	0.85255 (14)	0.6276 (2)	0.27963 (17)	0.0557 (7)
N1	0.46466 (14)	0.4872 (2)	0.16115 (13)	0.0261 (5)
N2	0.42919 (16)	0.7630 (2)	0.16733 (15)	0.0354 (6)
C1	0.38726 (18)	0.4299 (3)	0.13755 (18)	0.0335 (6)
H1	0.3503	0.4601	0.1620	0.040*
C2	0.3572 (2)	0.3272 (3)	0.07845 (19)	0.0393 (7)
H2	0.3019	0.2870	0.0647	0.047*
C3	0.40786 (19)	0.2856 (3)	0.04095 (18)	0.0358 (7)
H3	0.3877	0.2170	−0.0001	0.043*
C4	0.49061 (18)	0.3444 (3)	0.06280 (17)	0.0302 (6)
C5	0.5468 (2)	0.3055 (3)	0.02665 (18)	0.0374 (7)
H5	0.5291	0.2376	−0.0149	0.045*
C6	0.6262 (2)	0.3646 (3)	0.05078 (18)	0.0385 (7)
H6	0.6634	0.3376	0.0258	0.046*
C7	0.65411 (19)	0.4655 (3)	0.11237 (18)	0.0326 (6)
H7	0.7096	0.5065	0.1283	0.039*
C8	0.60136 (17)	0.5046 (3)	0.14920 (16)	0.0261 (5)
C9	0.51783 (17)	0.4455 (2)	0.12511 (16)	0.0248 (5)
C10	0.70390 (18)	0.6681 (3)	0.2358 (2)	0.0373 (7)
H10A	0.7064	0.7435	0.2729	0.045*
H10B	0.7081	0.7044	0.1854	0.045*
C11	0.78098 (18)	0.5763 (3)	0.2823 (2)	0.0382 (7)
C12	0.9318 (2)	0.5480 (5)	0.3221 (3)	0.0813 (16)
H12A	0.9430	0.5342	0.3810	0.122*
H12B	0.9817	0.5946	0.3200	0.122*
H12C	0.9239	0.4620	0.2937	0.122*
C13	0.39038 (18)	0.8424 (3)	0.11794 (17)	0.0283 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0251 (2)	0.0204 (2)	0.0262 (2)	0.000	0.00945 (19)	0.000
S1	0.0444 (5)	0.0390 (5)	0.0614 (6)	0.0141 (4)	0.0224 (4)	0.0225 (4)
O1	0.0250 (9)	0.0257 (10)	0.0394 (11)	−0.0032 (7)	0.0141 (8)	−0.0074 (8)
O2	0.0377 (12)	0.0420 (13)	0.0530 (14)	0.0062 (10)	0.0143 (11)	−0.0024 (11)
O3	0.0274 (11)	0.0552 (15)	0.0844 (18)	−0.0116 (10)	0.0241 (12)	−0.0261 (14)
N1	0.0240 (11)	0.0251 (11)	0.0270 (11)	0.0005 (9)	0.0091 (9)	0.0003 (9)
N2	0.0418 (14)	0.0276 (12)	0.0347 (13)	0.0042 (11)	0.0145 (12)	0.0037 (11)
C1	0.0265 (14)	0.0377 (16)	0.0355 (15)	−0.0048 (12)	0.0126 (12)	−0.0065 (13)
C2	0.0313 (15)	0.0437 (17)	0.0404 (17)	−0.0120 (13)	0.0131 (14)	−0.0094 (14)
C3	0.0399 (16)	0.0315 (15)	0.0295 (14)	−0.0057 (13)	0.0090 (13)	−0.0068 (12)
C4	0.0356 (15)	0.0262 (14)	0.0273 (13)	0.0033 (11)	0.0123 (12)	0.0017 (11)
C5	0.0478 (18)	0.0355 (16)	0.0303 (15)	0.0025 (14)	0.0182 (14)	−0.0043 (13)
C6	0.0439 (17)	0.0443 (18)	0.0345 (15)	0.0056 (14)	0.0238 (14)	−0.0013 (14)
C7	0.0310 (14)	0.0350 (15)	0.0336 (15)	0.0014 (12)	0.0157 (12)	0.0034 (12)
C8	0.0281 (13)	0.0227 (13)	0.0265 (13)	0.0033 (10)	0.0108 (11)	0.0034 (10)
C9	0.0276 (13)	0.0212 (13)	0.0235 (12)	0.0032 (10)	0.0092 (11)	0.0033 (10)
C10	0.0316 (15)	0.0275 (14)	0.0552 (19)	−0.0076 (12)	0.0211 (14)	−0.0064 (13)
C11	0.0268 (14)	0.0404 (17)	0.0454 (18)	−0.0040 (13)	0.0137 (13)	−0.0209 (15)
C12	0.0274 (18)	0.082 (3)	0.123 (4)	−0.0003 (19)	0.022 (2)	−0.045 (3)
C13	0.0304 (14)	0.0244 (14)	0.0343 (14)	0.0004 (11)	0.0180 (12)	−0.0011 (11)

Geometric parameters (Å, º)

Cu1—N2^i	1.950 (2)	C2—H2	0.9500
Cu1—N2	1.950 (2)	C3—C4	1.411 (4)
Cu1—N1	2.024 (2)	C3—H3	0.9500
Cu1—N1^i	2.024 (2)	C4—C5	1.410 (4)
Cu1—O1	2.4708 (19)	C4—C9	1.419 (4)
Cu1—O1^i	2.4708 (19)	C5—C6	1.358 (4)
S1—C13	1.621 (3)	C5—H5	0.9500
O1—C8	1.377 (3)	C6—C7	1.410 (4)
O1—C10	1.425 (3)	C6—H6	0.9500
O2—C11	1.192 (4)	C7—C8	1.368 (4)
O3—C11	1.336 (4)	C7—H7	0.9500
O3—C12	1.460 (5)	C8—C9	1.419 (4)
N1—C1	1.323 (3)	C10—C11	1.518 (4)
N1—C9	1.371 (3)	C10—H10A	0.9900
N2—C13	1.154 (3)	C10—H10B	0.9900
C1—C2	1.397 (4)	C12—H12A	0.9800
C1—H1	0.9500	C12—H12B	0.9800
C2—C3	1.354 (4)	C12—H12C	0.9800
N2^i—Cu1—N2	94.27 (15)	C3—C4—C9	117.6 (3)
N2^i—Cu1—N1	160.81 (9)	C6—C5—C4	120.4 (3)
N2—Cu1—N1	91.79 (10)	C6—C5—H5	119.8
N2^i—Cu1—N1^i	91.79 (10)	C4—C5—H5	119.8
N2—Cu1—N1^i	160.81 (9)	C5—C6—C7	120.9 (3)
N1—Cu1—N1^i	88.38 (12)	C5—C6—H6	119.6
N2^i—Cu1—O1	88.58 (9)	C7—C6—H6	119.6
N2—Cu1—O1	101.17 (9)	C8—C7—C6	120.1 (3)
N1—Cu1—O1	72.38 (7)	C8—C7—H7	120.0
N1^i—Cu1—O1	97.17 (8)	C6—C7—H7	120.0
N2^i—Cu1—O1^i	101.17 (9)	C7—C8—O1	125.0 (2)
N2—Cu1—O1^i	88.58 (9)	C7—C8—C9	120.5 (3)
N1—Cu1—O1^i	97.17 (8)	O1—C8—C9	114.5 (2)
N1^i—Cu1—O1^i	72.38 (7)	N1—C9—C8	120.1 (2)
C8—O1—C10	117.7 (2)	N1—C9—C4	121.2 (2)
C8—O1—Cu1	110.16 (15)	C8—C9—C4	118.7 (2)
C10—O1—Cu1	131.99 (16)	O1—C10—C11	111.7 (2)
C11—O3—C12	114.5 (3)	O1—C10—H10A	109.3
C1—N1—C9	118.7 (2)	C11—C10—H10A	109.3
C1—N1—Cu1	118.46 (19)	O1—C10—H10B	109.3
C9—N1—Cu1	122.87 (17)	C11—C10—H10B	109.3
C13—N2—Cu1	177.1 (2)	H10A—C10—H10B	107.9
N1—C1—C2	123.2 (3)	O2—C11—O3	125.6 (3)
N1—C1—H1	118.4	O2—C11—C10	125.4 (3)
C2—C1—H1	118.4	O3—C11—C10	109.0 (3)
C3—C2—C1	119.2 (3)	O3—C12—H12A	109.5
C3—C2—H2	120.4	O3—C12—H12B	109.5
C1—C2—H2	120.4	H12A—C12—H12B	109.5
C2—C3—C4	120.0 (3)	O3—C12—H12C	109.5
C2—C3—H3	120.0	H12A—C12—H12C	109.5
C4—C3—H3	120.0	H12B—C12—H12C	109.5
C5—C4—C3	123.0 (3)	N2—C13—S1	179.0 (3)
C5—C4—C9	119.4 (3)
N2^i—Cu1—O1—C8	178.32 (17)	C4—C5—C6—C7	0.1 (5)
N2—Cu1—O1—C8	−87.61 (17)	C5—C6—C7—C8	0.5 (4)
N1—Cu1—O1—C8	0.70 (15)	C6—C7—C8—O1	179.3 (2)
N1^i—Cu1—O1—C8	86.70 (16)	C6—C7—C8—C9	−0.9 (4)
N2^i—Cu1—O1—C10	−5.7 (2)	C10—O1—C8—C7	2.0 (4)
N2—Cu1—O1—C10	88.4 (2)	Cu1—O1—C8—C7	178.7 (2)
N1—Cu1—O1—C10	176.7 (2)	C10—O1—C8—C9	−177.8 (2)
N1^i—Cu1—O1—C10	−97.3 (2)	Cu1—O1—C8—C9	−1.1 (3)
N2^i—Cu1—N1—C1	171.9 (3)	C1—N1—C9—C8	−179.8 (2)
N2—Cu1—N1—C1	−79.7 (2)	Cu1—N1—C9—C8	−0.5 (3)
N1^i—Cu1—N1—C1	81.1 (2)	C1—N1—C9—C4	0.9 (4)
O1—Cu1—N1—C1	179.2 (2)	Cu1—N1—C9—C4	−179.83 (18)
N2^i—Cu1—N1—C9	−7.4 (4)	C7—C8—C9—N1	−178.7 (2)
N2—Cu1—N1—C9	101.0 (2)	O1—C8—C9—N1	1.2 (3)
N1^i—Cu1—N1—C9	−98.2 (2)	C7—C8—C9—C4	0.7 (4)
O1—Cu1—N1—C9	−0.11 (18)	O1—C8—C9—C4	−179.5 (2)
N2^i—Cu1—N2—C13	68 (5)	C5—C4—C9—N1	179.3 (2)
N1—Cu1—N2—C13	−94 (5)	C3—C4—C9—N1	−1.7 (4)
N1^i—Cu1—N2—C13	176 (100)	C5—C4—C9—C8	0.0 (4)
O1—Cu1—N2—C13	−21 (5)	C3—C4—C9—C8	179.0 (2)
C9—N1—C1—C2	1.0 (4)	C8—O1—C10—C11	−67.9 (3)
Cu1—N1—C1—C2	−178.3 (2)	Cu1—O1—C10—C11	116.3 (2)
N1—C1—C2—C3	−2.0 (5)	C12—O3—C11—O2	0.0 (5)
C1—C2—C3—C4	1.1 (5)	C12—O3—C11—C10	−179.8 (3)
C2—C3—C4—C5	179.7 (3)	O1—C10—C11—O2	−20.4 (4)
C2—C3—C4—C9	0.7 (4)	O1—C10—C11—O3	159.4 (2)
C3—C4—C5—C6	−179.3 (3)	Cu1—N2—C13—S1	72 (19)
C9—C4—C5—C6	−0.3 (4)

Symmetry code: (i) −x+1, y, −z+1/2.