catena-Poly[[aqua­(pyrazino[2,3-f][1,10]phenanthro­line-κ²N,N′)copper(II)]-μ-benzene-1,4-dicarboxyl­ato-κ²O¹:O⁴]

In the title compound, [Cu(C₈H₄O₄)(C₁₄H₈N₄)(H₂O)]_n, the Cu^II atom is five-coordinate and exhibits a distorted square-pyramidal coordination geometry. The benzene-1,4-dicarboxyl­ate ligand bridges the Cu^II atoms to form a one-dimensional chain structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.041
• wR factor = 0.122
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); 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: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL-Plus.

catena-Poly[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N,N')copper(II)]-µ- benzene-1,4-dicarboxylato-κ²O¹:O⁴]

Crystal data

[Cu(C8H4O4)(C14H8N4)(H2O)]	F(000) = 972
Mr = 477.91	Dx = 1.682 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 14313 reflections
a = 11.489 (2) Å	θ = 3.1–27.5°
b = 15.054 (3) Å	µ = 1.20 mm^−1
c = 12.186 (2) Å	T = 292 K
β = 116.40 (3)°	Block, blue
V = 1887.8 (8) Å^3	0.33 × 0.29 × 0.21 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	4258 independent reflections
Radiation source: rotation target	3427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.3°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −19→19
Tmin = 0.663, Tmax = 0.775	l = −14→15
17593 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0719P)^2 + 0.5273P] where P = (Fo^2 + 2Fc^2)/3
4258 reflections	(Δ/σ)max = 0.001
297 parameters	Δρmax = 0.78 e Å^−3
2 restraints	Δρmin = −0.50 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
C1	0.7332 (3)	0.1315 (2)	0.1950 (3)	0.0438 (6)
H1	0.8191	0.1351	0.2541	0.053*
C2	0.6960 (3)	0.1748 (2)	0.0829 (3)	0.0501 (7)
H2	0.7569	0.2070	0.0685	0.060*
C3	0.5696 (3)	0.1698 (2)	−0.0061 (3)	0.0465 (7)
H3	0.5443	0.1985	−0.0809	0.056*
C4	0.4793 (3)	0.12080 (17)	0.0176 (2)	0.0380 (6)
C5	0.5235 (3)	0.07986 (17)	0.1317 (2)	0.0329 (5)
C6	0.4358 (3)	0.03080 (16)	0.1645 (2)	0.0330 (5)
C7	0.4100 (3)	−0.0485 (2)	0.3143 (3)	0.0414 (6)
H7	0.4446	−0.0726	0.3927	0.050*
C8	0.2781 (3)	−0.0590 (2)	0.2381 (3)	0.0501 (7)
H8	0.2262	−0.0899	0.2658	0.060*
C9	0.2245 (3)	−0.0239 (2)	0.1224 (3)	0.0463 (7)
H9	0.1363	−0.0305	0.0710	0.056*
C10	0.3052 (3)	0.02218 (18)	0.0827 (2)	0.0371 (6)
C11	0.2585 (3)	0.06214 (19)	−0.0377 (2)	0.0394 (6)
C12	0.3433 (3)	0.10950 (18)	−0.0700 (2)	0.0395 (6)
C13	0.0940 (3)	0.0854 (2)	−0.2255 (3)	0.0566 (8)
H13	0.0078	0.0788	−0.2830	0.068*
C14	0.1779 (3)	0.1324 (2)	−0.2585 (3)	0.0565 (8)
H14	0.1449	0.1558	−0.3373	0.068*
C15	0.7913 (3)	−0.0997 (2)	0.5856 (3)	0.0419 (6)
C16	0.7754 (3)	−0.15184 (18)	0.6834 (2)	0.0386 (6)
C17	0.6542 (2)	−0.17430 (18)	0.6734 (2)	0.0356 (5)
H17	0.5797	−0.1568	0.6048	0.043*
C18	0.6435 (2)	−0.22260 (18)	0.7650 (2)	0.0352 (5)
H18	0.5616	−0.2376	0.7571	0.042*
C19	0.7535 (3)	−0.24917 (17)	0.8691 (2)	0.0360 (6)
C20	0.7393 (3)	−0.30972 (17)	0.9620 (2)	0.0354 (5)
C21	0.8750 (3)	−0.2246 (2)	0.8810 (3)	0.0464 (7)
H21	0.9492	−0.2407	0.9508	0.056*
C22	0.8864 (3)	−0.1763 (2)	0.7896 (3)	0.0484 (7)
H22	0.9682	−0.1599	0.7986	0.058*
N1	0.6482 (2)	0.08504 (15)	0.21921 (19)	0.0348 (5)
N2	0.4887 (2)	−0.00502 (15)	0.2789 (2)	0.0350 (5)
N3	0.3022 (3)	0.14565 (18)	−0.1839 (2)	0.0515 (6)
N4	0.1313 (3)	0.05022 (19)	−0.1171 (2)	0.0508 (6)
O1	0.68910 (19)	−0.06388 (15)	0.50352 (17)	0.0455 (5)
O2	0.9012 (2)	−0.0946 (2)	0.5914 (2)	0.0747 (8)
O1W	0.8644 (2)	0.03403 (15)	0.43798 (19)	0.0397 (4)
O3	0.83770 (18)	−0.35460 (14)	1.02995 (17)	0.0433 (5)
O4	0.62939 (19)	−0.31435 (14)	0.96002 (19)	0.0470 (5)
Cu1	0.67755 (3)	0.02134 (2)	0.37710 (3)	0.03297 (13)
H11W	0.900 (4)	−0.008 (2)	0.486 (4)	0.096 (17)*
H12W	0.873 (4)	0.0831 (16)	0.475 (3)	0.061 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0425 (16)	0.0453 (16)	0.0432 (15)	−0.0048 (12)	0.0188 (12)	0.0001 (12)
C2	0.0555 (19)	0.0486 (18)	0.0523 (17)	−0.0049 (14)	0.0296 (15)	0.0068 (13)
C3	0.0589 (19)	0.0444 (16)	0.0375 (15)	0.0024 (14)	0.0228 (13)	0.0066 (12)
C4	0.0489 (16)	0.0323 (13)	0.0323 (13)	0.0044 (11)	0.0177 (11)	0.0015 (10)
C5	0.0382 (14)	0.0295 (12)	0.0289 (12)	0.0037 (10)	0.0129 (10)	−0.0015 (9)
C6	0.0363 (14)	0.0295 (13)	0.0290 (12)	0.0027 (10)	0.0105 (10)	−0.0013 (9)
C7	0.0363 (15)	0.0456 (15)	0.0388 (14)	−0.0010 (12)	0.0137 (11)	0.0070 (11)
C8	0.0381 (17)	0.058 (2)	0.0493 (17)	−0.0067 (14)	0.0155 (13)	0.0114 (14)
C9	0.0354 (16)	0.0503 (18)	0.0432 (16)	−0.0035 (13)	0.0084 (12)	0.0025 (12)
C10	0.0371 (15)	0.0376 (14)	0.0323 (13)	0.0026 (11)	0.0115 (10)	−0.0003 (10)
C11	0.0401 (15)	0.0372 (14)	0.0314 (13)	0.0059 (11)	0.0073 (11)	−0.0003 (10)
C12	0.0482 (17)	0.0347 (14)	0.0280 (12)	0.0077 (12)	0.0102 (11)	−0.0008 (10)
C13	0.0500 (19)	0.063 (2)	0.0372 (16)	0.0056 (16)	0.0012 (13)	0.0017 (14)
C14	0.064 (2)	0.0560 (19)	0.0311 (15)	0.0099 (16)	0.0045 (14)	0.0055 (12)
C15	0.0355 (15)	0.0438 (16)	0.0423 (15)	0.0042 (12)	0.0135 (11)	0.0105 (12)
C16	0.0343 (14)	0.0385 (14)	0.0371 (14)	0.0011 (11)	0.0106 (11)	0.0054 (10)
C17	0.0292 (13)	0.0351 (13)	0.0321 (12)	0.0017 (10)	0.0043 (10)	0.0028 (10)
C18	0.0274 (13)	0.0380 (14)	0.0358 (13)	0.0000 (10)	0.0100 (10)	0.0008 (10)
C19	0.0375 (15)	0.0323 (13)	0.0328 (13)	0.0027 (11)	0.0106 (11)	0.0044 (10)
C20	0.0366 (14)	0.0348 (13)	0.0319 (13)	−0.0014 (11)	0.0126 (10)	−0.0011 (10)
C21	0.0276 (14)	0.0543 (18)	0.0434 (15)	0.0025 (12)	0.0033 (11)	0.0170 (13)
C22	0.0253 (14)	0.0592 (19)	0.0520 (17)	0.0009 (12)	0.0092 (12)	0.0208 (14)
N1	0.0343 (12)	0.0365 (12)	0.0325 (11)	0.0000 (9)	0.0140 (9)	−0.0011 (8)
N2	0.0340 (12)	0.0354 (11)	0.0303 (11)	0.0007 (9)	0.0096 (9)	0.0029 (8)
N3	0.0650 (18)	0.0464 (15)	0.0339 (12)	0.0042 (13)	0.0138 (12)	0.0049 (10)
N4	0.0421 (14)	0.0590 (16)	0.0394 (13)	0.0014 (12)	0.0073 (10)	0.0001 (11)
O1	0.0334 (10)	0.0570 (13)	0.0387 (10)	0.0012 (9)	0.0093 (8)	0.0161 (9)
O2	0.0432 (14)	0.097 (2)	0.0864 (17)	0.0199 (13)	0.0308 (12)	0.0544 (16)
O1W	0.0319 (10)	0.0454 (12)	0.0409 (11)	0.0027 (8)	0.0152 (8)	0.0029 (9)
O3	0.0305 (10)	0.0515 (12)	0.0421 (10)	0.0018 (8)	0.0109 (8)	0.0153 (9)
O4	0.0386 (11)	0.0506 (12)	0.0531 (12)	0.0082 (9)	0.0215 (9)	0.0117 (9)
Cu1	0.0292 (2)	0.0381 (2)	0.02807 (19)	0.00081 (12)	0.00948 (13)	0.00225 (11)

Geometric parameters (Å, º)

C1—N1	1.337 (3)	C13—H13	0.9300
C1—C2	1.398 (4)	C14—N3	1.323 (4)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.375 (4)	C15—O2	1.234 (4)
C2—H2	0.9300	C15—O1	1.275 (3)
C3—C4	1.404 (4)	C15—C16	1.504 (4)
C3—H3	0.9300	C16—C17	1.385 (4)
C4—C5	1.394 (3)	C16—C22	1.403 (4)
C4—C12	1.458 (4)	C17—C18	1.383 (4)
C5—N1	1.355 (3)	C17—H17	0.9300
C5—C6	1.442 (4)	C18—C19	1.393 (3)
C6—N2	1.360 (3)	C18—H18	0.9300
C6—C10	1.390 (4)	C19—C21	1.387 (4)
C7—N2	1.334 (4)	C19—C20	1.518 (3)
C7—C8	1.390 (4)	C20—O4	1.254 (3)
C7—H7	0.9300	C20—O3	1.260 (3)
C8—C9	1.369 (4)	C21—C22	1.384 (4)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.405 (4)	C22—H22	0.9300
C9—H9	0.9300	Cu1—N1	2.039 (2)
C10—C11	1.450 (4)	Cu1—N2	1.997 (2)
C11—N4	1.359 (4)	Cu1—O1	1.9634 (19)
C11—C12	1.397 (4)	Cu1—O1W	1.944 (2)
C12—N3	1.365 (3)	O1W—H11W	0.84 (4)
C13—N4	1.306 (4)	O1W—H12W	0.85 (2)
C13—C14	1.391 (5)	Cu1—O3^i	2.2311 (19)
N1—C1—C2	121.6 (3)	C17—C16—C22	118.8 (2)
N1—C1—H1	119.2	C17—C16—C15	122.0 (2)
C2—C1—H1	119.2	C22—C16—C15	119.2 (3)
C3—C2—C1	120.1 (3)	C18—C17—C16	120.3 (2)
C3—C2—H2	119.9	C18—C17—H17	119.9
C1—C2—H2	119.9	C16—C17—H17	119.9
C2—C3—C4	118.9 (3)	C17—C18—C19	121.0 (2)
C2—C3—H3	120.5	C17—C18—H18	119.5
C4—C3—H3	120.5	C19—C18—H18	119.5
C5—C4—C3	117.6 (3)	C21—C19—C18	118.8 (2)
C5—C4—C12	118.3 (3)	C21—C19—C20	121.3 (2)
C3—C4—C12	124.0 (3)	C18—C19—C20	119.7 (2)
N1—C5—C4	123.2 (3)	O4—C20—O3	125.7 (2)
N1—C5—C6	115.8 (2)	O4—C20—C19	117.4 (2)
C4—C5—C6	120.9 (2)	O3—C20—C19	116.7 (2)
N2—C6—C10	123.1 (3)	C22—C21—C19	120.4 (2)
N2—C6—C5	116.0 (2)	C22—C21—H21	119.8
C10—C6—C5	120.9 (2)	C19—C21—H21	119.8
N2—C7—C8	122.3 (3)	C21—C22—C16	120.6 (3)
N2—C7—H7	118.9	C21—C22—H22	119.7
C8—C7—H7	118.9	C16—C22—H22	119.7
C9—C8—C7	120.1 (3)	C1—N1—C5	118.5 (2)
C9—C8—H8	119.9	C1—N1—Cu1	128.62 (19)
C7—C8—H8	119.9	C5—N1—Cu1	112.90 (17)
C8—C9—C10	118.8 (3)	C7—N2—C6	117.9 (2)
C8—C9—H9	120.6	C7—N2—Cu1	128.01 (19)
C10—C9—H9	120.6	C6—N2—Cu1	114.03 (19)
C6—C10—C9	117.8 (3)	C14—N3—C12	114.8 (3)
C6—C10—C11	118.8 (3)	C13—N4—C11	115.6 (3)
C9—C10—C11	123.3 (3)	C15—O1—Cu1	127.54 (19)
N4—C11—C12	122.0 (2)	Cu1—O1W—H11W	108 (4)
N4—C11—C10	117.5 (3)	Cu1—O1W—H12W	98 (2)
C12—C11—C10	120.4 (3)	H11W—O1W—H12W	112 (4)
N3—C12—C11	121.4 (3)	C20—O3—Cu1^ii	122.17 (17)
N3—C12—C4	118.1 (3)	O1W—Cu1—O1	94.99 (9)
C11—C12—C4	120.5 (2)	O1W—Cu1—N2	165.78 (9)
N4—C13—C14	122.7 (3)	O1—Cu1—N2	90.96 (9)
N4—C13—H13	118.6	O1W—Cu1—N1	90.29 (9)
C14—C13—H13	118.6	O1—Cu1—N1	166.59 (9)
N3—C14—C13	123.5 (3)	N2—Cu1—N1	81.26 (9)
N3—C14—H14	118.2	O1W—Cu1—O3^i	92.68 (8)
C13—C14—H14	118.2	O1—Cu1—O3^i	98.15 (9)
O2—C15—O1	125.4 (3)	N2—Cu1—O3^i	99.26 (8)
O2—C15—C16	117.9 (3)	N1—Cu1—O3^i	93.90 (8)
O1—C15—C16	116.6 (2)
N1—C1—C2—C3	−0.4 (5)	C20—C19—C21—C22	173.9 (3)
C1—C2—C3—C4	0.0 (5)	C19—C21—C22—C16	−0.3 (5)
C2—C3—C4—C5	0.3 (4)	C17—C16—C22—C21	2.1 (5)
C2—C3—C4—C12	−179.0 (3)	C15—C16—C22—C21	−179.7 (3)
C3—C4—C5—N1	−0.2 (4)	C2—C1—N1—C5	0.5 (4)
C12—C4—C5—N1	179.1 (2)	C2—C1—N1—Cu1	−177.1 (2)
C3—C4—C5—C6	177.9 (2)	C4—C5—N1—C1	−0.2 (4)
C12—C4—C5—C6	−2.7 (4)	C6—C5—N1—C1	−178.4 (2)
N1—C5—C6—N2	−0.5 (3)	C4—C5—N1—Cu1	177.82 (19)
C4—C5—C6—N2	−178.8 (2)	C6—C5—N1—Cu1	−0.4 (3)
N1—C5—C6—C10	179.1 (2)	C8—C7—N2—C6	0.9 (4)
C4—C5—C6—C10	0.8 (4)	C8—C7—N2—Cu1	177.0 (2)
N2—C7—C8—C9	−0.2 (5)	C10—C6—N2—C7	−1.7 (4)
C7—C8—C9—C10	0.2 (5)	C5—C6—N2—C7	177.9 (2)
N2—C6—C10—C9	1.7 (4)	C10—C6—N2—Cu1	−178.3 (2)
C5—C6—C10—C9	−177.9 (2)	C5—C6—N2—Cu1	1.2 (3)
N2—C6—C10—C11	−179.4 (2)	C13—C14—N3—C12	−0.1 (5)
C5—C6—C10—C11	1.1 (4)	C11—C12—N3—C14	0.3 (4)
C8—C9—C10—C6	−0.9 (4)	C4—C12—N3—C14	179.7 (3)
C8—C9—C10—C11	−179.8 (3)	C14—C13—N4—C11	−0.2 (5)
C6—C10—C11—N4	177.9 (3)	C12—C11—N4—C13	0.4 (4)
C9—C10—C11—N4	−3.2 (4)	C10—C11—N4—C13	−178.4 (3)
C6—C10—C11—C12	−0.9 (4)	O2—C15—O1—Cu1	−8.8 (5)
C9—C10—C11—C12	178.0 (3)	C16—C15—O1—Cu1	170.79 (19)
N4—C11—C12—N3	−0.5 (4)	O4—C20—O3—Cu1^ii	18.0 (4)
C10—C11—C12—N3	178.3 (3)	C19—C20—O3—Cu1^ii	−157.97 (17)
N4—C11—C12—C4	−179.9 (3)	C15—O1—Cu1—O1W	−5.5 (3)
C10—C11—C12—C4	−1.1 (4)	C15—O1—Cu1—N2	161.5 (3)
C5—C4—C12—N3	−176.5 (2)	C15—O1—Cu1—N1	107.3 (4)
C3—C4—C12—N3	2.8 (4)	C15—O1—Cu1—O3^i	−99.0 (3)
C5—C4—C12—C11	2.9 (4)	C7—N2—Cu1—O1W	128.4 (4)
C3—C4—C12—C11	−177.8 (3)	C6—N2—Cu1—O1W	−55.3 (5)
N4—C13—C14—N3	0.1 (6)	C7—N2—Cu1—O1	13.6 (3)
O2—C15—C16—C17	−168.6 (3)	C6—N2—Cu1—O1	−170.15 (19)
O1—C15—C16—C17	11.8 (4)	C7—N2—Cu1—N1	−177.4 (3)
O2—C15—C16—C22	13.3 (5)	C6—N2—Cu1—N1	−1.12 (18)
O1—C15—C16—C22	−166.3 (3)	C7—N2—Cu1—O3^i	−84.8 (3)
C22—C16—C17—C18	−2.1 (4)	C6—N2—Cu1—O3^i	91.44 (19)
C15—C16—C17—C18	179.8 (3)	C1—N1—Cu1—O1W	−12.9 (2)
C16—C17—C18—C19	0.4 (4)	C5—N1—Cu1—O1W	169.34 (18)
C17—C18—C19—C21	1.4 (4)	C1—N1—Cu1—O1	−126.3 (4)
C17—C18—C19—C20	−174.0 (2)	C5—N1—Cu1—O1	56.0 (4)
C21—C19—C20—O4	165.7 (3)	C1—N1—Cu1—N2	178.6 (3)
C18—C19—C20—O4	−19.1 (4)	C5—N1—Cu1—N2	0.83 (17)
C21—C19—C20—O3	−18.0 (4)	C1—N1—Cu1—O3^i	79.8 (2)
C18—C19—C20—O3	157.2 (3)	C5—N1—Cu1—O3^i	−97.96 (18)
C18—C19—C21—C22	−1.4 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O2	0.84 (4)	1.83 (3)	2.593 (3)	151 (5)
O1W—H12W···O4^i	0.85 (2)	1.74 (2)	2.585 (3)	173 (4)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.