Bis(μ-salicylaldehyde semicarbazonato)bis­[formatocopper(II)]

The salicylaldehyde semicarbazonate anion O,N,O-chelates to the Cu atom in the title compound, bis­[μ-2-(semicarb­azono­meth­yl)phenolato]-1κ³O³,N¹,O:2κO;1κO:2κ³O³,N¹,O-bis­[(form­ato-κO)copper(II)] [Cu₂(C₈H₈N₃O₂)₂(CHO₂)₂], the N and O atoms occupying three sites of the square-planar environment around it. The fourth site is occupied by the negatively charged O atom of the formate anion. Two mol­ecules are bridged through the phen­oxy O atom across a center of symmetry to give a dinuclear compound, so that the Cu atom exists in a square-pyramidal geometry [Cu←O_phen­oxy = 2.546 (1) Å in the apical position]. Hydrogen bonds link the dinuclear mol­ecules into a three-dimensional network architecture.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.090
• Data-to-parameter ratio = 23.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H4     ..  H4      ..       2.03 Ang.

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1_a    ..       5.15 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Bis[µ-2-(semicarbazonomethyl)phenolato]- 1κ³O³,N¹,O:2κO;1κO:2κ³O³,N¹,O-bis[(formato-κO)copper(II)]

Crystal data

[Cu2(C8H8N3O2)2(CHO2)2]	F(000) = 580
Mr = 573.46	Dx = 1.835 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1754 reflections
a = 7.7562 (5) Å	θ = 2.6–32.0°
b = 14.1641 (8) Å	µ = 2.11 mm^−1
c = 9.6837 (6) Å	T = 173 K
β = 102.743 (1)°	Prism, green
V = 1037.6 (1) Å^3	0.33 × 0.11 × 0.07 mm
Z = 2

Data collection

Bruker SMART 1000 area-detector diffractometer	3551 independent reflections
Radiation source: fine-focus sealed tube	2997 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.33 pixels mm^-1	θmax = 32.0°, θmin = 2.6°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −21→20
Tmin = 0.675, Tmax = 0.866	l = −14→14
13226 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0459P)^2 + 0.5822P] where P = (Fo^2 + 2Fc^2)/3
3551 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.54 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.34785 (3)	0.50742 (1)	0.35372 (2)	0.01738 (7)
O1	0.3408 (2)	0.4413 (1)	0.5253 (1)	0.0213 (2)
O2	0.3463 (2)	0.5854 (1)	0.1843 (1)	0.0203 (2)
O3	0.4146 (2)	0.3927 (1)	0.2734 (1)	0.0214 (3)
O4	0.5353 (2)	0.3125 (1)	0.1236 (2)	0.0260 (3)
N1	0.2300 (2)	0.6166 (1)	0.4066 (2)	0.0184 (3)
N2	0.2159 (2)	0.6886 (1)	0.3089 (2)	0.0216 (3)
N3	0.2503 (2)	0.7260 (1)	0.0843 (2)	0.0240 (3)
C1	0.2459 (2)	0.4659 (1)	0.6179 (2)	0.0189 (3)
C2	0.2351 (2)	0.4016 (1)	0.7273 (2)	0.0237 (3)
C3	0.1459 (3)	0.4247 (2)	0.8319 (2)	0.0287 (4)
C4	0.0599 (3)	0.5114 (2)	0.8307 (2)	0.0309 (4)
C5	0.0667 (2)	0.5746 (2)	0.7239 (2)	0.0254 (4)
C6	0.1584 (2)	0.5540 (1)	0.6172 (2)	0.0194 (3)
C7	0.1561 (2)	0.6265 (1)	0.5128 (2)	0.0204 (3)
C8	0.2728 (2)	0.6644 (1)	0.1901 (2)	0.0181 (3)
C9	0.4956 (2)	0.3882 (1)	0.1718 (2)	0.0193 (3)
H2n	0.1741	0.7449	0.3219	0.026*
H3n1	0.2871	0.7123	0.0069	0.029*
H3n2	0.1986	0.7805	0.0915	0.029*
H2	0.2901	0.3416	0.7292	0.028*
H3	0.1431	0.3808	0.9055	0.034*
H4	−0.0019	0.5265	0.9023	0.037*
H5	0.0079	0.6335	0.7222	0.030*
H7	0.0976	0.6842	0.5225	0.025*
H9	0.5263	0.4453	0.1319	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0206 (1)	0.0153 (1)	0.0185 (1)	0.0030 (1)	0.0090 (1)	0.0020 (1)
O1	0.024 (1)	0.021 (1)	0.023 (1)	0.004 (1)	0.011 (1)	0.005 (1)
O2	0.024 (1)	0.018 (1)	0.022 (1)	0.005 (1)	0.011 (1)	0.002 (1)
O3	0.026 (1)	0.016 (1)	0.025 (1)	0.000 (1)	0.013 (1)	−0.001 (1)
O4	0.035 (1)	0.018 (1)	0.031 (1)	−0.003 (1)	0.018 (1)	−0.005 (1)
N1	0.022 (1)	0.017 (1)	0.018 (1)	0.002 (1)	0.008 (1)	0.003 (1)
N2	0.031 (1)	0.016 (1)	0.022 (1)	0.007 (1)	0.014 (1)	0.005 (1)
N3	0.034 (1)	0.018 (1)	0.024 (1)	0.006 (1)	0.014 (1)	0.005 (1)
C1	0.016 (1)	0.023 (1)	0.018 (1)	−0.002 (1)	0.004 (1)	0.003 (1)
C2	0.021 (1)	0.027 (1)	0.023 (1)	−0.003 (1)	0.005 (1)	0.006 (1)
C3	0.028 (1)	0.039 (1)	0.021 (1)	−0.004 (1)	0.008 (1)	0.009 (1)
C4	0.031 (1)	0.045 (1)	0.021 (1)	0.002 (1)	0.013 (1)	0.005 (1)
C5	0.025 (1)	0.035 (1)	0.019 (1)	0.004 (1)	0.010 (1)	0.001 (1)
C6	0.017 (1)	0.026 (1)	0.016 (1)	0.001 (1)	0.006 (1)	0.002 (1)
C7	0.022 (1)	0.022 (1)	0.019 (1)	0.004 (1)	0.008 (1)	0.000 (1)
C8	0.019 (1)	0.018 (1)	0.020 (1)	0.000 (1)	0.008 (1)	0.001 (1)
C9	0.022 (1)	0.016 (1)	0.021 (8)	−0.002 (1)	0.007 (1)	0.000 (1)

Geometric parameters (Å, º)

Cu1—O1	1.918 (1)	C2—C3	1.386 (3)
Cu1—O1^i	2.546 (1)	C3—C4	1.396 (3)
Cu1—O2	1.976 (1)	C4—C5	1.378 (3)
Cu1—O3	1.922 (1)	C5—C6	1.408 (2)
Cu1—N1	1.923 (1)	C6—C7	1.439 (2)
O1—C1	1.326 (2)	N2—H2n	0.88
O2—C8	1.262 (2)	N3—H3n1	0.88
O3—C9	1.280 (2)	N3—H3n2	0.88
O4—C9	1.234 (2)	C2—H2	0.95
N1—C7	1.290 (2)	C3—H3	0.95
N1—N2	1.380 (2)	C4—H4	0.95
N2—C8	1.364 (2)	C5—H5	0.95
N3—C8	1.328 (2)	C7—H7	0.95
C1—C2	1.413 (2)	C9—H9	0.95
C1—C6	1.419 (3)
O1—Cu1—O1^i	86.90 (5)	C5—C6—C7	116.0 (2)
O1—Cu1—O2	174.84 (5)	C1—C6—C7	124.2 (2)
O1—Cu1—O3	89.97 (5)	N1—C7—C6	122.9 (2)
O1—Cu1—N1	93.19 (6)	O2—C8—N3	122.1 (2)
O1^i—Cu1—O2	93.10 (5)	O2—C8—N2	119.6 (2)
O1^i—Cu1—O3	96.57 (5)	N3—C8—N2	118.3 (2)
O1^i—Cu1—N1	96.11 (5)	O4—C9—O3	122.7 (2)
O2—Cu1—O3	95.16 (5)	C8—N2—H2n	123.2
O2—Cu1—N1	81.67 (5)	N1—N2—H2n	123.2
O3—Cu1—N1	167.07 (6)	C8—N3—H3n1	120.0
C1—O1—Cu1	125.7 (1)	C8—N3—H3n2	120.0
C8—O2—Cu1	112.3 (1)	H3n1—N3—H3n2	120.0
C9—O3—Cu1	125.1 (1)	C3—C2—H2	119.4
C7—N1—N2	119.0 (1)	C1—C2—H2	119.4
C7—N1—Cu1	128.3 (1)	C2—C3—H3	119.5
N2—N1—Cu1	112.5 (1)	C4—C3—H3	119.5
C8—N2—N1	113.7 (1)	C5—C4—H4	120.6
O1—C1—C2	118.1 (2)	C3—C4—H4	120.6
O1—C1—C6	124.3 (2)	C4—C5—H5	119.2
C2—C1—C6	117.5 (2)	C6—C5—H5	119.2
C3—C2—C1	121.2 (2)	N1—C7—H7	118.5
C2—C3—C4	121.1 (2)	C6—C7—H7	118.5
C5—C4—C3	118.7 (2)	O4—C9—H9	118.7
C4—C5—C6	121.7 (2)	O3—C9—H9	118.7
C5—C6—C1	119.8 (2)
O3—Cu1—O1—C1	−154.9 (1)	Cu1—O1—C1—C6	−11.6 (2)
N1—Cu1—O1—C1	12.6 (2)	O1—C1—C2—C3	176.6 (2)
O1^i—Cu1—O1—C1	108.5 (2)	C6—C1—C2—C3	−1.4 (3)
O3—Cu1—O2—C8	167.0 (1)	C1—C2—C3—C4	1.5 (3)
N1—Cu1—O2—C8	−0.4 (1)	C2—C3—C4—C5	−0.6 (3)
O1^i—Cu1—O2—C8	−96.1 (1)	C3—C4—C5—C6	−0.4 (3)
O1—Cu1—O3—C9	−157.2 (2)	C4—C5—C6—C1	0.4 (3)
N1—Cu1—O3—C9	98.5 (3)	C4—C5—C6—C7	−179.5 (2)
O2—Cu1—O3—C9	23.4 (2)	O1—C1—C6—C5	−177.5 (2)
O1^i—Cu1—O3—C9	−70.3 (2)	C2—C1—C6—C5	0.5 (3)
O1—Cu1—N1—C7	−8.6 (2)	O1—C1—C6—C7	2.4 (3)
O3—Cu1—N1—C7	95.3 (3)	C2—C1—C6—C7	−179.6 (2)
O2—Cu1—N1—C7	171.9 (2)	N2—N1—C7—C6	177.7 (2)
O1^i—Cu1—N1—C7	−95.8 (2)	Cu1—N1—C7—C6	3.1 (3)
O1—Cu1—N1—N2	176.5 (1)	C5—C6—C7—N1	−177.9 (2)
O3—Cu1—N1—N2	−79.6 (3)	C1—C6—C7—N1	2.2 (3)
O2—Cu1—N1—N2	−3.0 (1)	Cu1—O2—C8—N3	−176.9 (2)
O1^i—Cu1—N1—N2	89.2 (1)	Cu1—O2—C8—N2	3.9 (2)
C7—N1—N2—C8	−169.7 (2)	N1—N2—C8—O2	−6.6 (2)
Cu1—N1—N2—C8	5.8 (2)	N1—N2—C8—N3	174.2 (2)
Cu1—O1—C1—C2	170.5 (1)	Cu1—O3—C9—O4	−179.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O4^ii	0.88	2.05	2.804 (2)	143
N3—H3n1···O4^iii	0.88	2.09	2.931 (2)	159
N3—H3n2···O1^ii	0.88	2.53	3.256 (2)	140
N3—H3n2···O3^ii	0.88	2.35	3.144 (2)	151

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