μ-Oxalato-κ⁴O¹,O²:O^1′,O^2′-bis­{[N,N′-bis­(pyridin-2-ylmethyl­ene)propane-1,2-diamine-κ⁴-N,N′,N′′,N′′′]copper(II)} bis­(perchlorate)

In the centrosymmetric dinuclear title complex, [Cu₂(C₂O₄)(C₁₅H₁₆N₄)₂](ClO₄)₂, each Cu^II ion is in an elongated octa­hedral environment, coordinated by two oxalate O atoms and four N atoms from the tetra­dentate ligand. One O atom and three N atoms are in the equatorial plane, and another O atom and one N atom are in axial sites. Each copper ion is bound to two O atoms from the two different carboxyl­ate groups of the oxalate ligands, with a Cu...Cu distance of 5.6623 (16) Å. The anions lie on twofold rotation axes.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.056
• wR factor = 0.147
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.14 Ratio

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT213_ALERT_2_C Atom C13     has ADP max/min Ratio .............       3.10 prola
PLAT214_ALERT_2_C Atom O3      (Anion/Solvent) ADP max/min Ratio         4.40 prola
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT323_ALERT_2_C Check Hybridisation of  Cl2    in Solvent/Ion             ?
PLAT324_ALERT_2_C Check for Possibly Missing H on Coordinating....         N2
PLAT324_ALERT_2_C Check for Possibly Missing H on Coordinating....         N3
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C16    -   C16_c  ...       1.55 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      91.00 A   3 

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
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          S
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cu          (2)       2.22

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: PROCESS-AUTO (Molecular Structure Corporation, 1994); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXTL (Bruker, 1997).

µ-Oxalato-κ⁴O¹,O²:O^1',O^2'-bis{[N,N'-bis(pyridin-2- ylmethylene)propane-1,2-diamine-κ⁴– N,N',N'',N''']copper(II)} bis(perchlorate)

Crystal data

[Cu2(C2O4)(C15H16N4)2](ClO4)2	F(000) = 936
Mr = 918.64	Dx = 1.506 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.339 (2) Å	Cell parameters from 16951 reflections
b = 9.2995 (19) Å	θ = 2.1–27.5°
c = 19.395 (4) Å	µ = 1.25 mm^−1
β = 97.79 (3)°	T = 293 K
V = 2026.3 (7) Å^3	Block, blue
Z = 2	0.40 × 0.25 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer	4599 independent reflections
Radiation source: fine-focus sealed tube	2290 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→14
Tmin = 0.694, Tmax = 0.829	k = 0→12
16951 measured reflections	l = −25→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0777P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.86	(Δ/σ)max = 0.001
4599 reflections	Δρmax = 0.64 e Å^−3
255 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (8)

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
Cu	0.19634 (4)	0.37228 (5)	0.58356 (2)	0.0448 (2)
Cl1	0.0000	0.7640 (2)	0.7500	0.0983 (7)
Cl2	0.5000	0.0344 (3)	0.7500	0.1450 (13)
O1	0.0168 (2)	0.6062 (3)	0.42796 (13)	0.0486 (7)
O2	0.1566 (2)	0.5045 (3)	0.50385 (13)	0.0483 (7)
O3	0.0830 (14)	0.8442 (12)	0.7554 (6)	0.490 (14)
O4	−0.0034 (6)	0.6869 (9)	0.6933 (3)	0.252 (4)
O5	0.5969 (6)	−0.0293 (8)	0.7532 (7)	0.321 (7)
O6	0.4778 (16)	0.1456 (14)	0.7154 (11)	0.568 (18)
N1	0.1779 (3)	0.1861 (4)	0.52937 (16)	0.0484 (8)
N2	0.2104 (3)	0.2341 (4)	0.66415 (15)	0.0490 (8)
N3	0.2147 (3)	0.5295 (4)	0.65839 (17)	0.0593 (10)
N4	0.3959 (3)	0.4299 (5)	0.5920 (2)	0.0673 (11)
C1	0.1838 (5)	0.1677 (5)	0.4610 (2)	0.0670 (14)
H1	0.1950	0.2475	0.4338	0.080*
C2	0.1737 (5)	0.0342 (6)	0.4306 (3)	0.0780 (15)
H2	0.1817	0.0235	0.3837	0.094*
C3	0.1521 (5)	−0.0808 (5)	0.4688 (3)	0.0692 (14)
H3	0.1443	−0.1716	0.4487	0.083*
C4	0.1417 (4)	−0.0629 (5)	0.5385 (3)	0.0667 (13)
H4	0.1253	−0.1411	0.5655	0.080*
C5	0.1562 (4)	0.0738 (5)	0.5676 (2)	0.0507 (10)
C6	0.1453 (4)	0.1036 (5)	0.6429 (2)	0.0657 (13)
H6	0.1035	0.0475	0.6710	0.079*
C7	0.1703 (4)	0.3177 (5)	0.7227 (2)	0.0596 (12)
H7	0.0856	0.3401	0.7105	0.071*
C8	0.2397 (4)	0.4573 (5)	0.7264 (2)	0.0623 (13)
H8A	0.2160	0.5184	0.7626	0.075*
H8B	0.3243	0.4379	0.7372	0.075*
C9	0.3108 (6)	0.6321 (6)	0.6465 (3)	0.0835 (17)
H9	0.3062	0.7313	0.6517	0.100*
C10	0.4174 (5)	0.5531 (7)	0.6247 (3)	0.0796 (17)
C11	0.5314 (7)	0.6157 (9)	0.6344 (4)	0.119 (3)
H11	0.5449	0.7028	0.6577	0.143*
C12	0.6208 (9)	0.5454 (15)	0.6090 (5)	0.164 (6)
H12	0.6975	0.5830	0.6150	0.197*
C13	0.5975 (7)	0.4225 (13)	0.5755 (4)	0.151 (5)
H13	0.6579	0.3753	0.5566	0.181*
C14	0.4847 (5)	0.3632 (7)	0.5683 (3)	0.0913 (19)
H14	0.4713	0.2748	0.5462	0.110*
C15	0.1864 (5)	0.2355 (6)	0.7919 (2)	0.0821 (16)
H15A	0.1403	0.1487	0.7870	0.123*
H15B	0.1602	0.2944	0.8275	0.123*
H15C	0.2690	0.2120	0.8045	0.123*
C16	0.0480 (3)	0.5328 (4)	0.47980 (18)	0.0395 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.0491 (3)	0.0456 (3)	0.0384 (3)	−0.0010 (3)	0.0012 (2)	0.0039 (2)
Cl1	0.150 (2)	0.0617 (12)	0.0959 (15)	0.000	0.0632 (15)	0.000
Cl2	0.092 (2)	0.0878 (18)	0.235 (4)	0.000	−0.048 (2)	0.000
O1	0.0474 (16)	0.0558 (17)	0.0421 (13)	−0.0009 (13)	0.0046 (12)	0.0132 (13)
O2	0.0394 (16)	0.0557 (17)	0.0490 (15)	−0.0056 (13)	0.0032 (12)	0.0151 (14)
O3	0.84 (3)	0.434 (14)	0.253 (9)	−0.52 (2)	0.264 (19)	−0.119 (14)
O4	0.204 (7)	0.346 (10)	0.187 (6)	0.172 (7)	−0.038 (5)	−0.134 (7)
O5	0.104 (5)	0.161 (6)	0.67 (2)	0.032 (5)	−0.049 (8)	0.102 (10)
O6	0.339 (17)	0.484 (15)	0.95 (5)	0.282 (17)	0.35 (2)	0.56 (3)
N1	0.055 (2)	0.0470 (19)	0.0427 (17)	−0.0030 (17)	0.0049 (16)	0.0017 (16)
N2	0.058 (2)	0.049 (2)	0.0399 (17)	−0.0033 (18)	0.0064 (16)	0.0075 (16)
N3	0.073 (3)	0.057 (2)	0.0431 (19)	0.000 (2)	−0.0079 (18)	−0.0080 (17)
N4	0.051 (3)	0.080 (3)	0.069 (3)	−0.002 (2)	0.001 (2)	0.023 (2)
C1	0.093 (4)	0.057 (3)	0.052 (3)	−0.014 (3)	0.015 (2)	−0.005 (2)
C2	0.093 (4)	0.082 (4)	0.060 (3)	−0.016 (3)	0.014 (3)	−0.025 (3)
C3	0.067 (3)	0.052 (3)	0.087 (4)	−0.006 (2)	0.002 (3)	−0.019 (3)
C4	0.063 (3)	0.046 (3)	0.088 (4)	−0.008 (2)	−0.001 (3)	0.011 (3)
C5	0.047 (3)	0.047 (2)	0.057 (2)	0.000 (2)	0.0027 (19)	0.003 (2)
C6	0.087 (4)	0.064 (3)	0.045 (2)	−0.021 (3)	0.003 (2)	0.016 (2)
C7	0.055 (3)	0.084 (3)	0.041 (2)	0.003 (3)	0.0092 (19)	0.001 (2)
C8	0.072 (3)	0.069 (3)	0.044 (2)	0.009 (3)	0.000 (2)	−0.007 (2)
C9	0.104 (5)	0.051 (3)	0.087 (4)	−0.014 (3)	−0.015 (3)	−0.002 (3)
C10	0.064 (4)	0.098 (4)	0.070 (3)	−0.025 (3)	−0.016 (3)	0.039 (3)
C11	0.093 (5)	0.153 (7)	0.097 (5)	−0.057 (5)	−0.039 (4)	0.055 (5)
C12	0.076 (6)	0.285 (16)	0.119 (8)	−0.066 (9)	−0.025 (6)	0.126 (9)
C13	0.051 (5)	0.289 (14)	0.116 (7)	0.045 (6)	0.021 (4)	0.130 (8)
C14	0.058 (4)	0.132 (5)	0.087 (4)	0.027 (4)	0.019 (3)	0.044 (4)
C15	0.108 (4)	0.100 (4)	0.039 (2)	−0.013 (3)	0.012 (2)	0.011 (3)
C16	0.045 (3)	0.036 (2)	0.0375 (19)	−0.0066 (18)	0.0041 (17)	−0.0016 (17)

Geometric parameters (Å, º)

Cu—O2	1.979 (3)	C2—C3	1.343 (7)
Cu—N2	2.013 (3)	C2—H2	0.930
Cu—N1	2.021 (3)	C3—C4	1.382 (7)
Cu—N3	2.051 (3)	C3—H3	0.930
Cu—N4	2.309 (4)	C4—C5	1.392 (6)
Cu—O1^i	2.405 (3)	C4—H4	0.930
Cl1—O3^ii	1.194 (9)	C5—C6	1.507 (6)
Cl1—O3	1.194 (9)	C6—H6	0.930
Cl1—O4	1.310 (6)	C7—C8	1.515 (6)
Cl1—O4^ii	1.310 (6)	C7—C15	1.533 (5)
Cl2—O6^iii	1.240 (10)	C7—H7	0.980
Cl2—O6	1.240 (10)	C8—H8A	0.970
Cl2—O5^iii	1.243 (7)	C8—H8B	0.970
Cl2—O5	1.243 (7)	C9—C10	1.523 (8)
O1—C16	1.227 (4)	C9—H9	0.930
O1—Cu^i	2.405 (3)	C10—C11	1.406 (8)
O2—C16	1.284 (4)	C11—C12	1.354 (13)
O6—O6^iii	1.37 (4)	C11—H11	0.930
N1—C5	1.323 (5)	C12—C13	1.323 (14)
N1—C1	1.347 (5)	C12—H12	0.930
N2—C6	1.451 (5)	C13—C14	1.382 (10)
N2—C7	1.497 (5)	C13—H13	0.930
N3—C8	1.473 (5)	C14—H14	0.930
N3—C9	1.489 (6)	C15—H15A	0.960
N4—C10	1.316 (7)	C15—H15B	0.960
N4—C14	1.318 (6)	C15—H15C	0.960
C1—C2	1.373 (6)	C16—C16^i	1.549 (7)
C1—H1	0.930
O2—Cu—N2	171.47 (12)	C4—C3—H3	120.3
O2—Cu—N1	97.43 (12)	C3—C4—C5	119.0 (5)
N2—Cu—N1	81.31 (13)	C3—C4—H4	120.5
O2—Cu—N3	95.76 (13)	C5—C4—H4	120.5
N2—Cu—N3	85.18 (14)	N1—C5—C4	121.0 (4)
N1—Cu—N3	166.43 (14)	N1—C5—C6	116.3 (4)
O2—Cu—N4	91.63 (12)	C4—C5—C6	122.7 (4)
N2—Cu—N4	96.84 (13)	N2—C6—C5	108.9 (4)
N1—Cu—N4	105.48 (16)	N2—C6—H6	125.5
N3—Cu—N4	77.26 (16)	C5—C6—H6	125.5
O2—Cu—O1^i	75.88 (10)	N2—C7—C8	105.7 (3)
N2—Cu—O1^i	95.65 (12)	N2—C7—C15	113.1 (4)
N1—Cu—O1^i	89.51 (12)	C8—C7—C15	112.7 (4)
N3—Cu—O1^i	90.62 (12)	N2—C7—H7	108.4
N4—Cu—O1^i	161.76 (13)	C8—C7—H7	108.4
O3^ii—Cl1—O3	102.7 (17)	C15—C7—H7	108.4
O3^ii—Cl1—O4	109.6 (8)	N3—C8—C7	108.2 (3)
O3—Cl1—O4	110.4 (7)	N3—C8—H8A	110.0
O3^ii—Cl1—O4^ii	110.4 (7)	C7—C8—H8A	110.0
O3—Cl1—O4^ii	109.6 (8)	N3—C8—H8B	110.0
O4—Cl1—O4^ii	113.6 (8)	C7—C8—H8B	110.0
O6^iii—Cl2—O6	67 (2)	H8A—C8—H8B	108.4
O6^iii—Cl2—O5^iii	122.6 (9)	N3—C9—C10	111.0 (4)
O6—Cl2—O5^iii	104.9 (10)	N3—C9—H9	124.5
O6^iii—Cl2—O5	104.9 (9)	C10—C9—H9	124.5
O6—Cl2—O5	122.6 (9)	N4—C10—C11	122.2 (7)
O5^iii—Cl2—O5	123.1 (7)	N4—C10—C9	116.8 (5)
C16—O1—Cu^i	107.3 (2)	C11—C10—C9	120.8 (7)
C16—O2—Cu	121.1 (2)	C12—C11—C10	118.1 (9)
Cl2—O6—O6^iii	56.5 (11)	C12—C11—H11	121.0
C5—N1—C1	119.2 (4)	C10—C11—H11	121.0
C5—N1—Cu	113.5 (3)	C13—C12—C11	119.1 (10)
C1—N1—Cu	127.3 (3)	C13—C12—H12	120.5
C6—N2—C7	117.0 (4)	C11—C12—H12	120.5
C6—N2—Cu	109.2 (2)	C12—C13—C14	121.0 (11)
C7—N2—Cu	104.9 (2)	C12—C13—H13	119.5
C8—N3—C9	112.0 (3)	C14—C13—H13	119.5
C8—N3—Cu	107.3 (3)	N4—C14—C13	121.1 (8)
C9—N3—Cu	110.7 (3)	N4—C14—H14	119.5
C10—N4—C14	118.5 (5)	C13—C14—H14	119.5
C10—N4—Cu	110.6 (4)	C7—C15—H15A	109.5
C14—N4—Cu	130.8 (4)	C7—C15—H15B	109.5
N1—C1—C2	121.8 (4)	H15A—C15—H15B	109.5
N1—C1—H1	119.1	C7—C15—H15C	109.5
C2—C1—H1	119.1	H15A—C15—H15C	109.5
C3—C2—C1	119.5 (4)	H15B—C15—H15C	109.5
C3—C2—H2	120.2	O1—C16—O2	124.6 (3)
C1—C2—H2	120.2	O1—C16—C16^i	119.3 (4)
C2—C3—C4	119.4 (5)	O2—C16—C16^i	116.1 (4)
C2—C3—H3	120.3

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