Aqua­bis(3-pyridylacrylato)-κ²O,O′;κO-bis­(3-pyridylmethanol-κN)copper(II)

In the title complex, [Cu(C₈H₆NO₂)₂(C₆H₇NO)₂(H₂O)], the Cu²⁺ ion has a highly distorted square-bipyramidal (4 + 1 + 1) coordination environment, and is bonded to three carboxyl­ate O atoms of two 3-pyridylacrylate anions (monodentate and asymetric bidentate), two pyridine N atoms of 3-pyridylmethanol ligands and one water O atom. O—H...O and O–H...N hydrogen bonds result in the formation of a two-dimensional layer structure.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.103
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O4
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.

   0 ALERT level A = In general: serious problem
   0 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: KappaCCD Software (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor 1997); data reduction: SCALEPACK and DENZO(Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Aquabis(3-pyridylacrylato)-κ²O,O';κO-bis(3-pyridylmethanol-κN)copper(II)

Crystal data

[Cu(C8H6NO2)2(C6H7NO)2(H2O)]	F(000) = 1236
Mr = 596.09	Dx = 1.434 Mg m^−3
Monoclinic, P21/n	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2yn	Cell parameters from 4231 reflections
a = 14.913 (2) Å	θ = 3.3–21.4°
b = 6.595 (1) Å	µ = 0.45 mm^−1
c = 28.081 (5) Å	T = 153 K
β = 91.749 (10)°	Prism, blue
V = 2760.5 (7) Å^3	0.40 × 0.40 × 0.35 mm
Z = 4

Data collection

Bruker–Nonius kappaCCD diffractometer	6306 independent reflections
Radiation source: fine-focus sealed tube	4574 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
ω and φ scans	θmax = 21.4°, θmin = 3.3°
Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997)	h = 0→19
Tmin = 0.840, Tmax = 0.858	k = −8→8
39231 measured reflections	l = −36→36

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0298P)^2 + 1.853P] where P = (Fo^2 + 2Fc^2)/3
6306 reflections	(Δ/σ)max = 0.004
436 parameters	Δρmax = 0.28 e Å^−3
23 restraints	Δρmin = −0.34 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)
Cu1	0.629261 (19)	0.79977 (5)	0.124032 (10)	0.04287 (11)
N4	0.5267 (5)	0.7073 (17)	0.0798 (3)	0.043 (2)	0.50
C23	0.4722 (9)	0.563 (2)	0.0957 (5)	0.040 (3)	0.50
H23	0.4906	0.4941	0.1241	0.048*	0.50
C24	0.3920 (18)	0.507 (6)	0.0745 (11)	0.052 (5)	0.50
C25	0.3750 (7)	0.5797 (16)	0.0298 (4)	0.076 (3)	0.50
H25	0.3222	0.5390	0.0126	0.091*	0.50
C26	0.4335 (6)	0.7111 (14)	0.0094 (3)	0.083 (2)	0.50
H26	0.4229	0.7596	−0.0221	0.099*	0.50
C27	0.5078 (5)	0.7708 (12)	0.0357 (2)	0.0662 (19)	0.50
H27	0.5481	0.8630	0.0216	0.079*	0.50
C28	0.3372 (10)	0.333 (2)	0.0930 (6)	0.087 (6)	0.50
H28A	0.3471	0.2126	0.0727	0.104*	0.50
H28B	0.3594	0.2990	0.1256	0.104*	0.50
O6	0.2453 (9)	0.370 (3)	0.0941 (6)	0.085 (5)	0.50
H6	0.2357	0.4651	0.1133	0.128*	0.50
N4'	0.5107 (5)	0.7366 (17)	0.0900 (3)	0.039 (2)	0.50
C23'	0.4579 (9)	0.586 (2)	0.1029 (6)	0.039 (3)	0.50
H23'	0.4724	0.5164	0.1317	0.047*	0.50
C24'	0.3831 (18)	0.525 (6)	0.0768 (11)	0.059 (8)	0.50
C25'	0.3534 (6)	0.6520 (14)	0.0413 (4)	0.065 (3)	0.50
H25'	0.2991	0.6232	0.0240	0.078*	0.50
C26'	0.4023 (4)	0.8208 (13)	0.0308 (3)	0.072 (2)	0.50
H26'	0.3816	0.9108	0.0064	0.086*	0.50
C27'	0.4809 (4)	0.8597 (12)	0.0553 (2)	0.0611 (18)	0.50
H27'	0.5149	0.9764	0.0476	0.073*	0.50
C28'	0.3285 (8)	0.3496 (19)	0.0957 (6)	0.087 (6)	0.50
H28C	0.3400	0.2260	0.0769	0.104*	0.50
H28D	0.3469	0.3221	0.1293	0.104*	0.50
O6'	0.2368 (7)	0.397 (3)	0.0928 (6)	0.089 (5)	0.50
H6'	0.2271	0.5004	0.1094	0.134*	0.50
N1	0.28910 (18)	1.1871 (5)	0.33885 (9)	0.0715 (7)
N2	0.96999 (16)	1.0315 (4)	−0.10247 (8)	0.0614 (6)
N3	0.73872 (13)	0.8851 (3)	0.16310 (7)	0.0416 (5)
O1	0.69516 (12)	0.8566 (3)	0.06663 (6)	0.0529 (5)
O2	0.76296 (16)	0.5549 (3)	0.06186 (8)	0.0767 (6)
O1W	0.66705 (13)	0.4621 (3)	0.13904 (7)	0.0591 (5)
H2W	0.6942	0.4543	0.1138	0.089*
H1W	0.6336	0.3669	0.1442	0.089*
O3	0.55490 (11)	0.8225 (3)	0.18063 (6)	0.0500 (4)
O4	0.54703 (14)	1.1393 (3)	0.15484 (7)	0.0635 (5)
O5	1.00215 (13)	1.2790 (4)	0.16916 (8)	0.0725 (6)
H5	1.0167	1.1811	0.1519	0.109*
C1	0.75227 (18)	0.7342 (5)	0.04965 (9)	0.0521 (7)
C2	0.81013 (19)	0.8167 (5)	0.01229 (9)	0.0556 (7)
H2	0.8385	0.7213	−0.0076	0.067*
C3	0.82581 (17)	1.0091 (4)	0.00415 (9)	0.0500 (6)
H3	0.7959	1.1053	0.0232	0.060*
C4	0.88600 (17)	1.0884 (4)	−0.03213 (9)	0.0465 (6)
C5	0.91514 (19)	0.9692 (4)	−0.06922 (9)	0.0559 (7)
H5A	0.8943	0.8332	−0.0709	0.067*
C6	0.9980 (2)	1.2224 (5)	−0.10027 (11)	0.0654 (8)
H6A	1.0377	1.2692	−0.1237	0.078*
C7	0.9726 (2)	1.3535 (5)	−0.06597 (12)	0.0729 (9)
H7	0.9934	1.4896	−0.0657	0.087*
C8	0.9159 (2)	1.2859 (5)	−0.03147 (11)	0.0636 (7)
H8	0.8975	1.3758	−0.0072	0.076*
C9	0.52702 (16)	1.0039 (4)	0.18354 (9)	0.0474 (6)
C10	0.46755 (17)	1.0463 (4)	0.22410 (9)	0.0525 (6)
H10	0.4536	0.9381	0.2449	0.063*
C11	0.43361 (18)	1.2256 (5)	0.23239 (10)	0.0546 (7)
H11	0.4498	1.3312	0.2113	0.066*
C12	0.37314 (17)	1.2817 (5)	0.27071 (9)	0.0537 (7)
C13	0.3456 (2)	1.1440 (5)	0.30476 (10)	0.0628 (8)
H13	0.3689	1.0100	0.3035	0.075*
C14	0.2585 (2)	1.3785 (6)	0.34041 (12)	0.0771 (10)
H14	0.2176	1.4129	0.3644	0.092*
C15	0.2829 (2)	1.5248 (6)	0.30969 (13)	0.0787 (10)
H15	0.2604	1.6589	0.3127	0.094*
C16	0.3403 (2)	1.4776 (5)	0.27411 (11)	0.0675 (8)
H16	0.3574	1.5783	0.2520	0.081*
C17	0.78755 (16)	1.0471 (4)	0.15192 (8)	0.0428 (5)
H17	0.7730	1.1163	0.1230	0.051*
C18	0.85802 (16)	1.1191 (4)	0.18009 (9)	0.0461 (6)
C19	0.87991 (18)	1.0136 (4)	0.22117 (9)	0.0541 (7)
H19	0.9285	1.0573	0.2413	0.065*
C20	0.83132 (19)	0.8455 (5)	0.23292 (9)	0.0563 (7)
H20	0.8459	0.7717	0.2612	0.068*
C21	0.76102 (18)	0.7848 (4)	0.20323 (9)	0.0500 (6)
H21	0.7274	0.6683	0.2115	0.060*
C22	0.9092 (2)	1.3064 (5)	0.16583 (12)	0.0689 (8)
H22A	0.8917	1.3428	0.1326	0.083*
H22B	0.8924	1.4207	0.1866	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03738 (16)	0.04410 (18)	0.04722 (17)	−0.00539 (14)	0.00249 (12)	0.00480 (14)
N4	0.034 (3)	0.052 (4)	0.043 (4)	−0.004 (3)	0.012 (3)	0.002 (3)
C23	0.031 (5)	0.047 (5)	0.041 (5)	0.005 (4)	0.005 (5)	−0.001 (4)
C24	0.047 (9)	0.044 (7)	0.064 (9)	−0.006 (6)	−0.003 (7)	−0.002 (6)
C25	0.064 (7)	0.073 (6)	0.091 (7)	−0.029 (5)	−0.021 (5)	0.000 (5)
C26	0.090 (6)	0.093 (6)	0.063 (4)	−0.022 (5)	−0.026 (4)	0.016 (4)
C27	0.067 (5)	0.076 (5)	0.055 (4)	−0.018 (4)	−0.006 (3)	0.018 (3)
C28	0.073 (9)	0.102 (11)	0.085 (8)	−0.035 (8)	0.011 (7)	−0.027 (7)
O6	0.103 (10)	0.081 (6)	0.072 (6)	−0.034 (6)	0.007 (6)	−0.004 (5)
N4'	0.032 (3)	0.053 (4)	0.033 (3)	0.003 (3)	0.013 (3)	0.004 (3)
C23'	0.033 (5)	0.038 (5)	0.046 (5)	−0.003 (4)	0.020 (3)	−0.002 (4)
C24'	0.036 (6)	0.070 (17)	0.070 (11)	−0.011 (7)	0.003 (6)	0.002 (9)
C25'	0.042 (4)	0.087 (8)	0.065 (5)	−0.003 (4)	−0.013 (3)	0.015 (5)
C26'	0.049 (4)	0.098 (6)	0.067 (4)	−0.010 (4)	−0.013 (3)	0.042 (4)
C27'	0.050 (4)	0.071 (5)	0.062 (4)	−0.016 (3)	−0.001 (3)	0.028 (4)
C28'	0.044 (7)	0.053 (6)	0.162 (15)	−0.022 (5)	−0.025 (7)	0.044 (8)
O6'	0.030 (4)	0.111 (10)	0.127 (10)	−0.029 (4)	0.014 (4)	−0.046 (7)
N1	0.0672 (16)	0.084 (2)	0.0641 (15)	0.0215 (15)	0.0136 (12)	0.0038 (14)
N2	0.0589 (14)	0.0670 (16)	0.0594 (14)	−0.0131 (12)	0.0201 (11)	−0.0071 (12)
N3	0.0380 (10)	0.0434 (11)	0.0436 (10)	−0.0025 (9)	0.0049 (8)	0.0021 (9)
O1	0.0507 (10)	0.0624 (12)	0.0459 (9)	−0.0055 (9)	0.0054 (8)	0.0047 (8)
O2	0.0888 (16)	0.0601 (14)	0.0828 (14)	−0.0031 (12)	0.0283 (12)	0.0094 (11)
O1W	0.0677 (12)	0.0413 (10)	0.0686 (12)	−0.0030 (9)	0.0055 (10)	0.0086 (9)
O3	0.0460 (10)	0.0446 (11)	0.0600 (10)	0.0001 (8)	0.0120 (8)	0.0051 (8)
O4	0.0666 (13)	0.0513 (11)	0.0735 (13)	−0.0045 (10)	0.0164 (10)	0.0129 (10)
O5	0.0532 (12)	0.0745 (15)	0.0907 (15)	−0.0248 (11)	0.0149 (11)	−0.0296 (12)
C1	0.0509 (15)	0.0590 (19)	0.0466 (14)	−0.0092 (13)	0.0027 (12)	−0.0044 (12)
C2	0.0588 (16)	0.0588 (18)	0.0499 (14)	−0.0007 (14)	0.0152 (12)	−0.0057 (13)
C3	0.0499 (15)	0.0535 (16)	0.0469 (13)	0.0014 (13)	0.0061 (11)	−0.0056 (12)
C4	0.0443 (14)	0.0475 (15)	0.0478 (13)	−0.0008 (12)	0.0031 (11)	−0.0004 (11)
C5	0.0601 (17)	0.0522 (17)	0.0563 (15)	−0.0117 (13)	0.0141 (13)	−0.0063 (13)
C6	0.0614 (18)	0.069 (2)	0.0669 (18)	−0.0150 (16)	0.0145 (15)	0.0081 (16)
C7	0.087 (2)	0.0472 (18)	0.086 (2)	−0.0154 (16)	0.0125 (19)	0.0024 (16)
C8	0.075 (2)	0.0508 (16)	0.0652 (17)	−0.0011 (16)	0.0100 (15)	−0.0044 (14)
C9	0.0360 (13)	0.0501 (16)	0.0561 (15)	−0.0068 (12)	0.0026 (11)	0.0025 (12)
C10	0.0481 (15)	0.0500 (16)	0.0596 (16)	−0.0003 (13)	0.0063 (12)	0.0064 (13)
C11	0.0499 (15)	0.0550 (17)	0.0587 (16)	−0.0003 (13)	−0.0007 (12)	0.0008 (13)
C12	0.0450 (14)	0.0622 (18)	0.0535 (15)	0.0040 (13)	−0.0058 (12)	−0.0051 (14)
C13	0.0602 (18)	0.0637 (19)	0.0648 (17)	0.0179 (15)	0.0078 (14)	0.0006 (15)
C14	0.069 (2)	0.092 (3)	0.070 (2)	0.028 (2)	0.0083 (16)	−0.0101 (19)
C15	0.080 (2)	0.073 (2)	0.083 (2)	0.0289 (19)	0.0009 (19)	−0.0080 (19)
C16	0.069 (2)	0.0610 (19)	0.0717 (19)	0.0132 (16)	−0.0036 (16)	−0.0022 (15)
C17	0.0410 (13)	0.0405 (14)	0.0471 (13)	−0.0002 (11)	0.0062 (10)	0.0003 (11)
C18	0.0391 (13)	0.0410 (14)	0.0587 (15)	−0.0009 (11)	0.0080 (11)	−0.0107 (12)
C19	0.0448 (14)	0.0622 (18)	0.0549 (15)	−0.0016 (13)	−0.0038 (12)	−0.0144 (14)
C20	0.0550 (16)	0.069 (2)	0.0450 (14)	0.0057 (14)	−0.0032 (12)	0.0043 (13)
C21	0.0492 (14)	0.0504 (15)	0.0509 (14)	−0.0049 (13)	0.0085 (12)	0.0072 (12)
C22	0.0615 (18)	0.0543 (18)	0.091 (2)	−0.0192 (16)	0.0033 (16)	−0.0102 (16)

Geometric parameters (Å, º)

Cu1—O1	1.9495 (17)	O1W—H2W	0.8277
Cu1—O3	1.9713 (17)	O1W—H1W	0.8173
Cu1—N3	2.0188 (19)	O3—C9	1.270 (3)
Cu1—N4'	2.027 (8)	O4—C9	1.245 (3)
Cu1—N4	2.035 (8)	O5—C22	1.398 (4)
Cu1—O1W	2.3324 (18)	O5—H5	0.8400
N4—C27	1.328 (9)	C1—C2	1.482 (4)
N4—C23	1.336 (10)	C2—C3	1.312 (4)
C23—C24	1.372 (10)	C2—H2	0.9500
C23—H23	0.9500	C3—C4	1.474 (3)
C24—C25	1.362 (14)	C3—H3	0.9500
C24—C28	1.510 (11)	C4—C8	1.376 (4)
C25—C26	1.367 (10)	C4—C5	1.385 (4)
C25—H25	0.9500	C5—H5A	0.9500
C26—C27	1.370 (8)	C6—C7	1.357 (4)
C26—H26	0.9500	C6—H6A	0.9500
C27—H27	0.9500	C7—C8	1.379 (4)
C28—O6	1.394 (11)	C7—H7	0.9500
C28—H28A	0.9900	C8—H8	0.9500
C28—H28B	0.9900	C9—C10	1.491 (4)
O6—H6	0.8400	C10—C11	1.310 (4)
N4'—C23'	1.324 (10)	C10—H10	0.9500
N4'—C27'	1.333 (10)	C11—C12	1.472 (4)
C23'—C24'	1.375 (11)	C11—H11	0.9500
C23'—H23'	0.9500	C12—C16	1.386 (4)
C24'—C25'	1.364 (14)	C12—C13	1.390 (4)
C24'—C28'	1.522 (10)	C13—H13	0.9500
C25'—C26'	1.368 (10)	C14—C15	1.351 (5)
C25'—H25'	0.9500	C14—H14	0.9500
C26'—C27'	1.367 (8)	C15—C16	1.372 (4)
C26'—H26'	0.9500	C15—H15	0.9500
C27'—H27'	0.9500	C16—H16	0.9500
C28'—O6'	1.403 (11)	C17—C18	1.380 (3)
C28'—H28C	0.9900	C17—H17	0.9500
C28'—H28D	0.9900	C18—C19	1.378 (4)
O6'—H6'	0.8400	C18—C22	1.512 (4)
N1—C13	1.326 (4)	C19—C20	1.370 (4)
N1—C14	1.344 (4)	C19—H19	0.9500
N2—C5	1.325 (3)	C20—C21	1.379 (4)
N2—C6	1.328 (4)	C20—H20	0.9500
N3—C17	1.335 (3)	C21—H21	0.9500
N3—C21	1.340 (3)	C22—H22A	0.9900
O1—C1	1.276 (3)	C22—H22B	0.9900
O2—C1	1.240 (3)
O1—Cu1—O3	164.18 (8)	H2W—O1W—H1W	114.9
O1—Cu1—N3	88.63 (8)	C9—O3—Cu1	108.49 (16)
O3—Cu1—N3	90.35 (8)	C22—O5—H5	109.5
O1—Cu1—N4'	96.0 (2)	O2—C1—O1	125.5 (3)
O3—Cu1—N4'	83.8 (2)	O2—C1—C2	118.3 (3)
N3—Cu1—N4'	173.0 (3)	O1—C1—C2	116.2 (3)
O1—Cu1—N4	86.6 (2)	C3—C2—C1	126.1 (3)
O3—Cu1—N4	94.8 (2)	C3—C2—H2	116.9
N3—Cu1—N4	174.7 (2)	C1—C2—H2	116.9
N4'—Cu1—N4	12.0 (4)	C2—C3—C4	125.4 (2)
O1—Cu1—O1W	101.99 (7)	C2—C3—H3	117.3
O3—Cu1—O1W	93.78 (7)	C4—C3—H3	117.3
N3—Cu1—O1W	88.92 (8)	C8—C4—C5	116.0 (2)
N4'—Cu1—O1W	95.3 (3)	C8—C4—C3	122.0 (2)
N4—Cu1—O1W	89.8 (3)	C5—C4—C3	122.0 (2)
C27—N4—C23	115.0 (8)	N2—C5—C4	124.7 (3)
C27—N4—Cu1	127.5 (7)	N2—C5—H5A	117.7
C23—N4—Cu1	117.5 (7)	C4—C5—H5A	117.7
N4—C23—C24	125.3 (10)	N2—C6—C7	122.9 (3)
N4—C23—H23	117.3	N2—C6—H6A	118.6
C24—C23—H23	117.3	C7—C6—H6A	118.6
C25—C24—C23	116.1 (11)	C6—C7—C8	118.9 (3)
C25—C24—C28	119.8 (13)	C6—C7—H7	120.6
C23—C24—C28	122.1 (10)	C8—C7—H7	120.6
C24—C25—C26	120.4 (9)	C4—C8—C7	120.1 (3)
C24—C25—H25	119.8	C4—C8—H8	119.9
C26—C25—H25	119.8	C7—C8—H8	119.9
C25—C26—C27	118.2 (7)	O4—C9—O3	123.3 (2)
C25—C26—H26	120.9	O4—C9—C10	121.3 (3)
C27—C26—H26	120.9	O3—C9—C10	115.4 (2)
N4—C27—C26	123.8 (7)	C11—C10—C9	123.2 (3)
N4—C27—H27	118.1	C11—C10—H10	118.4
C26—C27—H27	118.1	C9—C10—H10	118.4
O6—C28—C24	114.5 (16)	C10—C11—C12	127.3 (3)
O6—C28—H28A	108.6	C10—C11—H11	116.4
C24—C28—H28A	108.6	C12—C11—H11	116.4
O6—C28—H28B	108.6	C16—C12—C13	116.7 (3)
C24—C28—H28B	108.6	C16—C12—C11	120.7 (3)
H28A—C28—H28B	107.6	C13—C12—C11	122.6 (3)
C23'—N4'—C27'	117.9 (9)	N1—C13—C12	124.3 (3)
C23'—N4'—Cu1	122.9 (8)	N1—C13—H13	117.8
C27'—N4'—Cu1	119.1 (7)	C12—C13—H13	117.8
N4'—C23'—C24'	123.6 (11)	N1—C14—C15	123.5 (3)
N4'—C23'—H23'	118.2	N1—C14—H14	118.2
C24'—C23'—H23'	118.2	C15—C14—H14	118.2
C25'—C24'—C23'	116.8 (14)	C14—C15—C16	119.3 (3)
C25'—C24'—C28'	123.8 (10)	C14—C15—H15	120.4
C23'—C24'—C28'	118.0 (10)	C16—C15—H15	120.4
C24'—C25'—C26'	119.5 (9)	C15—C16—C12	119.4 (3)
C24'—C25'—H25'	120.2	C15—C16—H16	120.3
C26'—C25'—H25'	120.2	C12—C16—H16	120.3
C27'—C26'—C25'	119.9 (6)	N3—C17—C18	123.5 (2)
C27'—C26'—H26'	120.1	N3—C17—H17	118.3
C25'—C26'—H26'	120.1	C18—C17—H17	118.3
N4'—C27'—C26'	121.1 (6)	C19—C18—C17	117.6 (2)
N4'—C27'—H27'	119.5	C19—C18—C22	121.7 (2)
C26'—C27'—H27'	119.5	C17—C18—C22	120.7 (2)
O6'—C28'—C24'	109.9 (14)	C20—C19—C18	119.8 (2)
O6'—C28'—H28C	109.7	C20—C19—H19	120.1
C24'—C28'—H28C	109.7	C18—C19—H19	120.1
O6'—C28'—H28D	109.7	C19—C20—C21	119.2 (3)
C24'—C28'—H28D	109.7	C19—C20—H20	120.4
H28C—C28'—H28D	108.2	C21—C20—H20	120.4
C28'—O6'—H6'	109.5	N3—C21—C20	122.0 (3)
C13—N1—C14	116.7 (3)	N3—C21—H21	119.0
C5—N2—C6	117.5 (3)	C20—C21—H21	119.0
C17—N3—C21	118.0 (2)	O5—C22—C18	112.6 (3)
C17—N3—Cu1	122.21 (16)	O5—C22—H22A	109.1
C21—N3—Cu1	119.68 (17)	C18—C22—H22A	109.1
C1—O1—Cu1	123.12 (17)	O5—C22—H22B	109.1
Cu1—O1W—H2W	91.5	C18—C22—H22B	109.1
Cu1—O1W—H1W	128.4	H22A—C22—H22B	107.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2^i	0.84	1.99	2.814 (3)	168
O6—H6···N1^ii	0.84	2.03	2.87 (2)	178
O6′—H6′···N1^ii	0.84	1.93	2.75 (2)	165
O1W—H2W···O2	0.83	1.93	2.703 (3)	156
O1W—H1W···O4^iii	0.82	2.01	2.825 (3)	177

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