Bis[μ-4,4′-methyl­enebis(3-hydr­oxy-2-naphthoato-κ²O:O′)]bis­[aqua­(ethyl­enediamine-κ²N,N′)copper(II)]

The title complex, [Cu₂(C₂₃H₁₄O₆)₂(C₂H₈N₂)₂(H₂O)₂], is composed of discrete centrosymmetric mol­ecular dimers, with each Cu^II atom in a slightly distorted square-pyramidal coordination geometry. The Cu^II atom is coordinated by two N atoms from an ethyl­enediamine mol­ecule, two O atoms from two pamoate ligands and one water O atom. The dimers are linked via hydrogen bonds, forming a two-dimensional supra­molecular network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.150
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O7W     ..       7.20 su
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2B    ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

Bis[µ-4,4'-methylenebis(3-hydroxy-2-naphthoato- κ²O:O')]bis[aqua(ethylenediamine-κ²N,N')copper(II)]

Crystal data

[Cu2(C23H14O6)2(C2H8N2)2(H2O)2]	F(000) = 1092
Mr = 1056.02	Dx = 1.568 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14451 reflections
a = 12.379 (3) Å	θ = 3.1–27.5°
b = 21.425 (4) Å	µ = 1.03 mm^−1
c = 8.8420 (18) Å	T = 293 K
β = 107.45 (3)°	Block, blue
V = 2237.2 (9) Å^3	0.37 × 0.16 × 0.14 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	5108 independent reflections
Radiation source: fine-focus sealed tube	3613 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −16→16
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	k = −27→27
Tmin = 0.704, Tmax = 0.870	l = −11→11
21559 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
5108 reflections	(Δ/σ)max = 0.021
322 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.74 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	0.44074 (3)	0.110447 (18)	1.04011 (4)	0.03396 (15)
O1	0.5425 (2)	0.10981 (12)	0.9104 (3)	0.0461 (6)
O2	0.6493 (2)	0.02635 (10)	1.0042 (3)	0.0433 (6)
O3	0.80515 (18)	−0.00427 (9)	0.8893 (2)	0.0316 (5)
H30	0.7728	−0.0012	0.9575	0.038*
O4	0.7841 (2)	−0.02863 (9)	0.3652 (2)	0.0387 (5)
H4	0.7499	−0.0426	0.2776	0.046*
O5	0.68815 (19)	−0.11295 (10)	0.1562 (2)	0.0374 (5)
O6	0.6570 (2)	−0.20795 (11)	0.2393 (3)	0.0438 (6)
O7W	0.4635 (2)	0.22641 (12)	1.0741 (3)	0.0474 (6)
H7WA	0.428 (4)	0.2429 (19)	1.123 (5)	0.057*
H7WB	0.420 (4)	0.2316 (19)	0.976 (5)	0.057*
N1	0.5556 (2)	0.07895 (13)	1.2336 (3)	0.0346 (6)
H1A	0.6065	0.1091	1.2754	0.042*
H1B	0.5927	0.0462	1.2088	0.042*
N2	0.3418 (2)	0.11901 (13)	1.1821 (3)	0.0375 (6)
H2A	0.2853	0.0909	1.1548	0.045*
H2B	0.3111	0.1574	1.1720	0.045*
C1	0.6226 (3)	0.07294 (14)	0.9144 (3)	0.0299 (6)
C2	0.6848 (2)	0.08467 (13)	0.7961 (3)	0.0242 (6)
C3	0.6595 (2)	0.13556 (13)	0.6972 (3)	0.0257 (6)
H3A	0.6042	0.1634	0.7065	0.031*
C4	0.7150 (2)	0.14675 (12)	0.5824 (3)	0.0250 (6)
C5	0.6885 (3)	0.19974 (13)	0.4818 (4)	0.0338 (7)
H5	0.6368	0.2289	0.4960	0.041*
C6	0.7376 (3)	0.20857 (15)	0.3647 (4)	0.0389 (7)
H6	0.7196	0.2435	0.2996	0.047*
C7	0.8154 (3)	0.16464 (14)	0.3430 (4)	0.0381 (7)
H7	0.8479	0.1706	0.2619	0.046*
C8	0.8447 (3)	0.11356 (13)	0.4377 (4)	0.0320 (7)
H8	0.8971	0.0854	0.4209	0.038*
C9	0.7960 (2)	0.10248 (12)	0.5625 (3)	0.0244 (6)
C10	0.8253 (2)	0.05033 (12)	0.6670 (3)	0.0238 (5)
C11	0.7721 (2)	0.04347 (12)	0.7830 (3)	0.0236 (6)
C12	0.9178 (2)	0.00469 (12)	0.6633 (3)	0.0277 (6)
H12A	0.9746	0.0052	0.7663	0.033*
H12B	0.9538	0.0195	0.5865	0.033*
C13	0.7015 (3)	−0.15538 (14)	0.2632 (4)	0.0322 (7)
C14	0.7781 (2)	−0.13917 (14)	0.4250 (3)	0.0274 (6)
C15	0.8133 (3)	−0.18586 (14)	0.5330 (3)	0.0300 (6)
H15	0.7887	−0.2264	0.5041	0.036*
C16	0.8853 (2)	−0.17483 (13)	0.6860 (3)	0.0281 (6)
C17	0.9261 (3)	−0.22494 (15)	0.7933 (4)	0.0345 (7)
H17	0.9043	−0.2656	0.7616	0.041*
C18	0.9961 (3)	−0.21430 (16)	0.9414 (4)	0.0427 (8)
H18	1.0231	−0.2475	1.0100	0.051*
C19	1.0278 (3)	−0.15324 (16)	0.9906 (4)	0.0419 (8)
H19	1.0748	−0.1462	1.0931	0.050*
C20	0.9913 (3)	−0.10384 (15)	0.8916 (4)	0.0346 (7)
H20	1.0140	−0.0638	0.9279	0.042*
C21	0.9198 (2)	−0.11213 (12)	0.7349 (3)	0.0264 (6)
C22	0.8810 (2)	−0.06262 (13)	0.6226 (3)	0.0251 (6)
C23	0.8156 (2)	−0.07678 (12)	0.4711 (3)	0.0264 (6)
C24	0.4978 (3)	0.05975 (16)	1.3485 (3)	0.0399 (8)
H24A	0.5518	0.0560	1.4534	0.048*
H24B	0.4612	0.0197	1.3188	0.048*
C25	0.4117 (3)	0.10865 (19)	1.3483 (4)	0.0499 (10)
H25A	0.3643	0.0950	1.4116	0.060*
H25B	0.4491	0.1471	1.3932	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0260 (2)	0.0561 (3)	0.0226 (2)	0.00727 (16)	0.01160 (15)	0.00347 (16)
O1	0.0402 (14)	0.0727 (17)	0.0342 (12)	0.0234 (12)	0.0246 (11)	0.0147 (11)
O2	0.0529 (16)	0.0470 (13)	0.0413 (13)	0.0106 (11)	0.0315 (12)	0.0087 (11)
O3	0.0356 (13)	0.0345 (11)	0.0290 (10)	0.0054 (9)	0.0162 (9)	0.0046 (9)
O4	0.0508 (15)	0.0350 (11)	0.0267 (11)	0.0064 (10)	0.0061 (10)	0.0050 (9)
O5	0.0319 (12)	0.0516 (14)	0.0250 (10)	0.0029 (10)	0.0030 (9)	0.0027 (10)
O6	0.0454 (15)	0.0454 (13)	0.0337 (12)	−0.0054 (11)	0.0013 (11)	−0.0085 (10)
O7W	0.0480 (17)	0.0481 (14)	0.0432 (14)	−0.0059 (12)	0.0094 (12)	−0.0029 (12)
N1	0.0343 (15)	0.0487 (15)	0.0221 (12)	0.0027 (11)	0.0104 (11)	−0.0025 (11)
N2	0.0313 (15)	0.0514 (16)	0.0362 (14)	−0.0047 (12)	0.0198 (12)	−0.0046 (12)
C1	0.0257 (15)	0.0427 (17)	0.0234 (13)	−0.0004 (12)	0.0104 (12)	−0.0039 (13)
C2	0.0220 (14)	0.0294 (14)	0.0222 (13)	−0.0023 (10)	0.0083 (11)	−0.0060 (11)
C3	0.0242 (15)	0.0274 (14)	0.0269 (14)	0.0015 (11)	0.0096 (11)	−0.0073 (12)
C4	0.0273 (15)	0.0246 (13)	0.0231 (13)	−0.0026 (11)	0.0073 (11)	−0.0034 (11)
C5	0.0370 (18)	0.0282 (14)	0.0375 (16)	0.0040 (12)	0.0130 (14)	0.0011 (13)
C6	0.043 (2)	0.0339 (16)	0.0400 (17)	−0.0006 (14)	0.0133 (15)	0.0101 (14)
C7	0.044 (2)	0.0396 (17)	0.0372 (17)	−0.0046 (14)	0.0227 (15)	0.0035 (14)
C8	0.0304 (16)	0.0336 (15)	0.0372 (16)	−0.0005 (12)	0.0180 (13)	−0.0015 (13)
C9	0.0229 (14)	0.0271 (13)	0.0254 (13)	−0.0022 (11)	0.0102 (11)	−0.0025 (11)
C10	0.0196 (13)	0.0267 (13)	0.0260 (13)	−0.0027 (10)	0.0081 (11)	−0.0059 (11)
C11	0.0221 (14)	0.0233 (12)	0.0261 (13)	−0.0023 (10)	0.0086 (11)	−0.0036 (11)
C12	0.0254 (15)	0.0304 (14)	0.0307 (14)	0.0014 (11)	0.0137 (12)	−0.0019 (12)
C13	0.0239 (15)	0.0426 (17)	0.0304 (15)	0.0066 (13)	0.0087 (12)	−0.0043 (13)
C14	0.0229 (15)	0.0340 (15)	0.0252 (14)	0.0039 (11)	0.0071 (11)	−0.0021 (12)
C15	0.0276 (16)	0.0310 (14)	0.0311 (15)	0.0010 (11)	0.0081 (12)	−0.0020 (12)
C16	0.0246 (15)	0.0303 (14)	0.0298 (14)	−0.0006 (11)	0.0090 (12)	0.0000 (12)
C17	0.0339 (17)	0.0356 (16)	0.0328 (16)	−0.0027 (13)	0.0083 (13)	0.0053 (13)
C18	0.039 (2)	0.0458 (19)	0.0375 (17)	−0.0012 (15)	0.0029 (15)	0.0166 (15)
C19	0.0371 (19)	0.052 (2)	0.0295 (15)	−0.0046 (15)	0.0000 (14)	0.0056 (15)
C20	0.0297 (17)	0.0399 (16)	0.0313 (15)	−0.0025 (13)	0.0047 (13)	−0.0046 (13)
C21	0.0213 (14)	0.0324 (15)	0.0282 (14)	0.0025 (11)	0.0114 (11)	−0.0013 (12)
C22	0.0219 (14)	0.0285 (13)	0.0278 (13)	0.0038 (11)	0.0121 (11)	−0.0008 (11)
C23	0.0254 (15)	0.0298 (14)	0.0267 (14)	0.0074 (11)	0.0118 (11)	0.0000 (11)
C24	0.051 (2)	0.0452 (18)	0.0220 (14)	−0.0165 (15)	0.0091 (14)	0.0009 (14)
C25	0.046 (2)	0.082 (3)	0.0309 (17)	−0.0103 (19)	0.0247 (16)	−0.0099 (17)

Geometric parameters (Å, º)

Cu1—O1	1.941 (2)	C7—C8	1.359 (4)
Cu1—O5^i	1.975 (2)	C7—H7	0.9300
Cu1—N1	1.986 (3)	C8—C9	1.427 (4)
Cu1—N2	2.007 (3)	C8—H8	0.9300
Cu1—O7W	2.508 (3)	C9—C10	1.425 (4)
O1—C1	1.260 (4)	C10—C11	1.383 (4)
O2—C1	1.256 (4)	C10—C12	1.514 (4)
O3—C11	1.366 (3)	C12—C22	1.523 (4)
O3—H30	0.8201	C12—H12A	0.9700
O4—C23	1.369 (3)	C12—H12B	0.9700
O4—H4	0.8200	C13—C14	1.501 (4)
O5—C13	1.286 (4)	C14—C15	1.361 (4)
O5—Cu1^i	1.975 (2)	C14—C23	1.433 (4)
O6—C13	1.244 (4)	C15—C16	1.399 (4)
O7W—H7WA	0.79 (4)	C15—H15	0.9300
O7W—H7WB	0.88 (4)	C16—C17	1.421 (4)
N1—C24	1.467 (4)	C16—C21	1.436 (4)
N1—H1A	0.9000	C17—C18	1.355 (5)
N1—H1B	0.9001	C17—H17	0.9300
N2—C25	1.482 (5)	C18—C19	1.397 (5)
N2—H2A	0.9000	C18—H18	0.9300
N2—H2B	0.9002	C19—C20	1.361 (5)
C1—C2	1.495 (4)	C19—H19	0.9300
C2—C3	1.374 (4)	C20—C21	1.414 (4)
C2—C11	1.427 (4)	C20—H20	0.9300
C3—C4	1.406 (4)	C21—C22	1.434 (4)
C3—H3A	0.9300	C22—C23	1.376 (4)
C4—C5	1.419 (4)	C24—C25	1.493 (5)
C4—C9	1.429 (4)	C24—H24A	0.9700
C5—C6	1.362 (4)	C24—H24B	0.9700
C5—H5	0.9300	C25—H25A	0.9700
C6—C7	1.400 (5)	C25—H25B	0.9700
C6—H6	0.9300
O1—Cu1—O5^i	88.70 (10)	C11—C10—C12	118.6 (2)
O1—Cu1—N1	94.73 (10)	C9—C10—C12	122.6 (2)
O5^i—Cu1—N1	161.31 (10)	O3—C11—C10	118.6 (2)
O1—Cu1—N2	174.55 (12)	O3—C11—C2	119.0 (2)
O5^i—Cu1—N2	93.65 (11)	C10—C11—C2	122.3 (3)
N1—Cu1—N2	84.61 (11)	C10—C12—C22	116.2 (2)
O1—Cu1—O7W	90.48 (10)	C10—C12—H12A	108.2
O5^i—Cu1—O7W	96.34 (9)	C22—C12—H12A	108.2
N1—Cu1—O7W	101.99 (10)	C10—C12—H12B	108.2
N2—Cu1—O7W	84.38 (10)	C22—C12—H12B	108.2
C1—O1—Cu1	129.2 (2)	H12A—C12—H12B	107.4
C11—O3—H30	109.6	O6—C13—O5	124.2 (3)
C23—O4—H4	109.4	O6—C13—C14	119.5 (3)
C13—O5—Cu1^i	123.9 (2)	O5—C13—C14	116.3 (3)
Cu1—O7W—H7WA	117 (3)	C15—C14—C23	118.5 (3)
Cu1—O7W—H7WB	90 (3)	C15—C14—C13	118.4 (3)
H7WA—O7W—H7WB	102 (4)	C23—C14—C13	123.0 (3)
C24—N1—Cu1	108.6 (2)	C14—C15—C16	122.1 (3)
C24—N1—H1A	110.1	C14—C15—H15	119.0
Cu1—N1—H1A	110.0	C16—C15—H15	119.0
C24—N1—H1B	109.9	C15—C16—C17	120.9 (3)
Cu1—N1—H1B	109.9	C15—C16—C21	119.6 (3)
H1A—N1—H1B	108.3	C17—C16—C21	119.4 (3)
C25—N2—Cu1	108.8 (2)	C18—C17—C16	120.9 (3)
C25—N2—H2A	110.0	C18—C17—H17	119.5
Cu1—N2—H2A	110.0	C16—C17—H17	119.5
C25—N2—H2B	109.8	C17—C18—C19	119.8 (3)
Cu1—N2—H2B	109.9	C17—C18—H18	120.1
H2A—N2—H2B	108.3	C19—C18—H18	120.1
O1—C1—O2	124.8 (3)	C20—C19—C18	121.3 (3)
O1—C1—C2	116.2 (3)	C20—C19—H19	119.4
O2—C1—C2	118.9 (3)	C18—C19—H19	119.4
C3—C2—C11	118.2 (2)	C19—C20—C21	121.5 (3)
C3—C2—C1	120.8 (3)	C19—C20—H20	119.3
C11—C2—C1	121.0 (2)	C21—C20—H20	119.3
C2—C3—C4	121.8 (3)	C20—C21—C22	124.5 (3)
C2—C3—H3A	119.1	C20—C21—C16	117.0 (3)
C4—C3—H3A	119.1	C22—C21—C16	118.4 (3)
C3—C4—C5	121.2 (3)	C23—C22—C21	119.2 (3)
C3—C4—C9	119.2 (3)	C23—C22—C12	119.1 (2)
C5—C4—C9	119.5 (3)	C21—C22—C12	121.5 (2)
C6—C5—C4	121.1 (3)	O4—C23—C22	117.6 (2)
C6—C5—H5	119.5	O4—C23—C14	120.5 (3)
C4—C5—H5	119.5	C22—C23—C14	121.9 (2)
C5—C6—C7	119.5 (3)	N1—C24—C25	107.4 (3)
C5—C6—H6	120.2	N1—C24—H24A	110.2
C7—C6—H6	120.2	C25—C24—H24A	110.2
C8—C7—C6	121.6 (3)	N1—C24—H24B	110.2
C8—C7—H7	119.2	C25—C24—H24B	110.2
C6—C7—H7	119.2	H24A—C24—H24B	108.5
C7—C8—C9	120.9 (3)	N2—C25—C24	108.1 (3)
C7—C8—H8	119.5	N2—C25—H25A	110.1
C9—C8—H8	119.5	C24—C25—H25A	110.1
C10—C9—C8	123.2 (3)	N2—C25—H25B	110.1
C10—C9—C4	119.5 (2)	C24—C25—H25B	110.1
C8—C9—C4	117.4 (3)	H25A—C25—H25B	108.4
C11—C10—C9	118.6 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7W—H7WA···O6^ii	0.79 (4)	2.11 (4)	2.898 (4)	176 (4)
O7W—H7WB···O6^i	0.88 (4)	1.92 (4)	2.753 (4)	156 (4)
N2—H2A···O3^iii	0.90	2.14	3.011 (3)	162
O3—H30···O2	0.82	1.80	2.522 (3)	146
O4—H4···O5	0.82	1.88	2.602 (3)	147

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