The binuclear copper(II) complex μ-chloro-μ-methoxy-bis­[chloro­(di-2-pyridyl­amine)copper(II)]

In the title binuclear copper(II) complex, [Cu₂Cl₃(CH₃O)(C₁₀H₉N₃)₂], the metal centers adopt distorted trigonal bipyramidal five-coordinate geometry. The mol­ecule possesses a C₂ axis, on which lie the bridging Cl⁻ anion and the methoxy group. The non-bridging coordinated Cl⁻ ions participate in N—H...Cl and C—H...Cl inter- and intramolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.096
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT707_ALERT_1_A D...A   Calc   20.101(3), Rep    3.188(3), Dev..    5637.67 Sigma
              N2   -CL2     1.555   3.566
PLAT707_ALERT_1_A D...A   Calc   21.591(4), Rep    3.717(4), Dev..    4468.50 Sigma
              C3   -CL1     1.555   5.445
PLAT726_ALERT_1_A H...A   Calc    19.71690, Rep     2.32000, Dev..      17.40 Ang.
              H2A  -CL2     1.555   3.566
PLAT726_ALERT_1_A H...A   Calc    21.10100, Rep     2.83000, Dev..      18.27 Ang.
              H3A  -CL1     1.555   5.445
PLAT728_ALERT_1_A D-H..A  Calc      114.67, Rep      170.00, Dev.       55.33 Deg.
              N2   -H2A  -CL2     1.555   1.555   3.566
PLAT728_ALERT_1_A D-H..A  Calc      119.91, Rep      156.00, Dev.       36.09 Deg.
              C3   -H3A  -CL1     1.555   1.555   5.445

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

   6 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

µ-chloro-µ-methoxy-bis[chloro(di-2-pyridylamine)copper(II)]

Crystal data

[Cu2Cl3(CH3O)(C10H9N3)2]	F(000) = 1224
Mr = 606.87	Dx = 1.750 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from all reflections
a = 16.9245 (3) Å	θ = 2.3–27.5°
b = 7.6655 (2) Å	µ = 2.22 mm^−1
c = 19.2417 (4) Å	T = 150 K
β = 112.6724 (9)°	Plate, green
V = 2303.41 (9) Å^3	0.10 × 0.10 × 0.02 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2633 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan Blessing, 1995	h = −21→21
Tmin = 0.836, Tmax = 0.965	k = −9→9
9609 measured reflections	l = −24→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 3.9941P] where P = (Fo^2 + 2Fc^2)/3
2633 reflections	(Δ/σ)max = 0.001
152 parameters	Δρmax = 0.81 e Å^−3
0 restraints	Δρmin = −0.54 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	Occ. (<1)
Cu	0.01537 (2)	0.55208 (5)	0.33904 (2)	0.02169 (15)
Cl1	0.0000	0.79493 (15)	0.2500	0.0251 (3)
Cl2	0.13860 (5)	0.38716 (12)	0.40850 (5)	0.0285 (2)
O1	0.0000	0.4194 (4)	0.2500	0.0224 (7)
N1	−0.10866 (16)	0.5208 (4)	0.33323 (15)	0.0206 (6)
N2	−0.08074 (16)	0.6477 (4)	0.45286 (15)	0.0236 (6)
H2A	−0.1004	0.6500	0.4891	0.028*
N3	0.04158 (16)	0.7120 (4)	0.42653 (15)	0.0240 (6)
C1	−0.1664 (2)	0.4450 (5)	0.27081 (19)	0.0252 (7)
H1A	−0.1484	0.4127	0.2316	0.030*
C2	−0.2497 (2)	0.4125 (5)	0.2613 (2)	0.0270 (8)
H2B	−0.2876	0.3543	0.2175	0.032*
C3	−0.2776 (2)	0.4663 (5)	0.31709 (19)	0.0267 (8)
H3A	−0.3354	0.4486	0.3112	0.032*
C4	−0.2210 (2)	0.5449 (5)	0.38045 (19)	0.0256 (8)
H4A	−0.2387	0.5820	0.4193	0.031*
C5	−0.1359 (2)	0.5702 (4)	0.38714 (18)	0.0207 (7)
C6	−0.0009 (2)	0.7218 (4)	0.47249 (18)	0.0224 (7)
C7	0.0337 (2)	0.8075 (5)	0.54221 (18)	0.0264 (7)
H7A	0.0031	0.8103	0.5745	0.032*
C8	0.1119 (2)	0.8870 (5)	0.5634 (2)	0.0313 (8)
H8A	0.1367	0.9432	0.6110	0.038*
C9	0.1549 (2)	0.8844 (5)	0.5141 (2)	0.0349 (9)
H9A	0.2081	0.9430	0.5262	0.042*
C10	0.1181 (2)	0.7953 (5)	0.4483 (2)	0.0305 (8)
H10A	0.1478	0.7910	0.4153	0.037*
C11	0.0000	0.2346 (7)	0.2500	0.0363 (13)
H11A	−0.0087	0.1920	0.1995	0.054*	0.50
H11B	−0.0463	0.1920	0.2642	0.054*	0.50
H11C	0.0550	0.1920	0.2863	0.054*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0155 (2)	0.0314 (3)	0.0187 (2)	−0.00132 (17)	0.00716 (16)	−0.00178 (17)
Cl1	0.0241 (6)	0.0278 (6)	0.0224 (6)	0.000	0.0077 (5)	0.000
Cl2	0.0190 (4)	0.0456 (5)	0.0210 (4)	0.0057 (3)	0.0077 (3)	0.0022 (4)
O1	0.0203 (16)	0.0259 (18)	0.0221 (17)	0.000	0.0093 (13)	0.000
N1	0.0172 (13)	0.0281 (15)	0.0168 (13)	−0.0003 (11)	0.0069 (11)	0.0014 (12)
N2	0.0198 (14)	0.0359 (17)	0.0179 (14)	−0.0014 (12)	0.0104 (11)	−0.0018 (12)
N3	0.0192 (14)	0.0318 (16)	0.0214 (15)	−0.0021 (12)	0.0083 (12)	−0.0005 (12)
C1	0.0217 (16)	0.0326 (19)	0.0208 (17)	0.0002 (15)	0.0077 (14)	−0.0003 (15)
C2	0.0228 (17)	0.0288 (19)	0.0247 (18)	−0.0036 (14)	0.0039 (14)	0.0010 (15)
C3	0.0158 (16)	0.036 (2)	0.0286 (19)	−0.0003 (14)	0.0093 (14)	0.0060 (16)
C4	0.0186 (16)	0.036 (2)	0.0245 (18)	0.0063 (15)	0.0113 (14)	0.0033 (16)
C5	0.0189 (16)	0.0248 (17)	0.0195 (16)	0.0022 (13)	0.0087 (13)	0.0039 (14)
C6	0.0184 (16)	0.0231 (17)	0.0205 (17)	0.0033 (13)	0.0018 (13)	0.0023 (14)
C7	0.0290 (18)	0.0286 (19)	0.0191 (17)	0.0039 (15)	0.0067 (14)	0.0007 (15)
C8	0.0302 (19)	0.029 (2)	0.0242 (19)	−0.0003 (15)	−0.0013 (15)	−0.0030 (16)
C9	0.0216 (18)	0.037 (2)	0.038 (2)	−0.0063 (16)	0.0038 (16)	−0.0003 (18)
C10	0.0242 (18)	0.038 (2)	0.030 (2)	−0.0051 (16)	0.0103 (15)	−0.0007 (17)
C11	0.033 (3)	0.035 (3)	0.036 (3)	0.000	0.009 (2)	0.000

Geometric parameters (Å, º)

Cu—O1	1.9220 (17)	C4—C5	1.408 (4)
Cu—N3	1.990 (3)	C6—C7	1.403 (5)
Cu—N1	2.072 (3)	C7—C8	1.368 (5)
Cu—Cl2	2.3633 (9)	C8—C9	1.402 (5)
Cu—Cl1	2.4748 (10)	C9—C10	1.360 (5)
Cl1—Cu^i	2.4748 (10)	N2—H2A	0.8810
O1—C11	1.416 (6)	C1—H1A	0.9490
O1—Cu^i	1.9220 (17)	C2—H2B	0.9508
N1—C5	1.342 (4)	C3—H3A	0.9501
N1—C1	1.353 (4)	C4—H4A	0.9498
N2—C6	1.378 (4)	C7—H7A	0.9501
N2—C5	1.383 (4)	C8—H8A	0.9509
N3—C6	1.339 (4)	C9—H9A	0.9514
N3—C10	1.356 (4)	C10—H10A	0.9503
C1—C2	1.374 (5)	C11—H11A	0.9809
C2—C3	1.391 (5)	C11—H11B	0.9800
C3—C4	1.367 (5)	C11—H11C	0.9797
O1—Cu—N3	171.81 (10)	N2—C6—C7	117.3 (3)
O1—Cu—N1	96.00 (8)	C8—C7—C6	119.5 (3)
N3—Cu—N1	90.44 (11)	C7—C8—C9	119.1 (3)
O1—Cu—Cl2	90.44 (6)	C10—C9—C8	117.7 (3)
N3—Cu—Cl2	89.47 (8)	N3—C10—C9	124.4 (3)
N1—Cu—Cl2	128.56 (8)	C5—N2—H2A	113.86
O1—Cu—Cl1	80.73 (8)	C6—N2—H2A	113.86
N3—Cu—Cl1	92.97 (9)	N1—C1—H1A	118.33
N1—Cu—Cl1	102.45 (7)	C2—C1—H1A	118.34
Cl2—Cu—Cl1	128.92 (3)	C1—C2—H2B	120.71
Cu^i—Cl1—Cu	82.44 (4)	C3—C2—H2B	120.62
C11—O1—Cu	121.95 (8)	C2—C3—H3A	120.37
C11—O1—Cu^i	121.95 (8)	C4—C3—H3A	120.33
Cu—O1—Cu^i	116.09 (16)	C3—C4—H4A	120.60
C5—N1—C1	117.5 (3)	C5—C4—H4A	120.55
C5—N1—Cu	124.7 (2)	C6—C7—H7A	120.27
C1—N1—Cu	117.9 (2)	C8—C7—H7A	120.22
C6—N2—C5	132.3 (3)	C7—C8—H8A	120.38
C6—N3—C10	117.4 (3)	C9—C8—H8A	120.47
C6—N3—Cu	126.3 (2)	C8—C9—H9A	121.15
C10—N3—Cu	115.2 (2)	C10—C9—H9A	121.04
N1—C1—C2	123.3 (3)	N3—C10—H10A	117.71
C1—C2—C3	118.7 (3)	C9—C10—H10A	117.98
C4—C3—C2	119.3 (3)	O1—C11—H11A	109.44
C3—C4—C5	118.9 (3)	O1—C11—H11B	109.46
N1—C5—N2	121.0 (3)	O1—C11—H11C	109.47
N1—C5—C4	122.3 (3)	H11A—C11—H11B	109.54
N2—C5—C4	116.7 (3)	H11A—C11—H11C	109.50
N3—C6—N2	121.0 (3)	H11B—C11—H11C	109.41
N3—C6—C7	121.7 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2^ii	0.88	2.32	3.188 (3)	170
C1—H1A···Cl2^i	0.95	2.77	3.684 (4)	162
C1—H1A···O1	0.95	2.40	3.000 (4)	121
C3—H3A···Cl1^iii	0.95	2.83	3.717 (4)	156
C9—H9A···Cl2^iv	0.95	2.74	3.672 (4)	168
C11—H11A···Cl2^i	0.98	2.80	3.264 (2)	109
C11—H11C···Cl2	0.98	2.68	3.264 (2)	118

Symmetry codes: (i) −x, y, −z+1/2; (ii) x+1/2, y+3/2, z+1; (iii) −x−1, −y−1, −z; (iv) −x+1/2, −y+3/2, −z+1.