catena-Poly[[bis­(4-methoxy­benzoato)copper(II)]-μ-1,1′-(oxydiethyl­ene)diimidazole-κ²N³:N^3′]

In the title compound, [Cu(C₇H₄O₃)₂(C₁₀H₁₄N₄O)]_n, the Cu^II atom lies on a centre of symmetry and is four-coordinated by two N atoms from two 1,1′-(oxydiethyl­ene)diimidazole (BIE) ligands and two O atoms from two 4-methoxy­benzoate anions in a square-planar geometry. Each BIE ligand links two Cu^II atoms to form an infinite chain structure along the c axis. The 4-methoxy­benzoate anion, as a terminal ligand, attaches to both sides of the BIE–Cu^II chains.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• H-atom completeness 72%
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.155
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           572.06
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   26.00  312.29
           H         1.01   20.00   20.16
           N        14.01    4.00   56.03
           O        16.00    7.00  111.99
           Cu       63.55    1.00   63.55
           Calculated formula weight              564.01
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     572.06
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C1      ..       2.98 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C26 H28 Cu1 N4 O7
            Atom count from the _atom_site data:  C26 H20 Cu1 N4 O7
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C26 H28 Cu N4 O7
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        104.00    104.00    0.00
           H        112.00     80.00   32.00
           Cu         4.00      4.00    0.00
           N         16.00     16.00    0.00
           O         28.00     28.00    0.00
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
   8 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   9 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
   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

---

S1. Comment

Coordination polymers constructed by substituted benzimidazole or imidazole have received increasing interests (Yang et al., 2006; Ma et al., 2000). We have selected 2,2'-bis(imidazol)ether (BIE) as a bridging ligand, p-methoxybenzoate as an anion, and Cu^II as a central metal, generating a new chain coordination polymer, [Cu(p-MB)₂(BIE)]_n, (I), which is reported here. In this structure the Cu^II atom lies on a centre of symmetry and is four-coordinated by two nitrogen atoms from two BIE molecules and two oxygen atoms from two different p-MB anions (Cu–N 2.003 (3) Å and Cu–O 1.980 (2) Å) in a square-planar coordination geometry (Fig. 1). The Cu–O and Cu–N bond lengths are all within normal ranges (Zhang et al., 2004; Cao et al., 2002). The two nitrogen atoms of the BIE ligand bridge two Cu^II centers, leading to a one-dimensional chain structure (Fig. 2). The monocarboxylate p-MB anion, as a terminal ligand, attaches to both sides of the BIE-Cu^II chains.

Related literature

For related literature, see: Cao et al. (2002); Ma et al. (2000); Yang et al. (2006); Zhang et al. (2004).

S2. Experimental

A mixture of CuCl₂.2H₂O (86.0 mg, 0.5 mmol) and NaOH (40 mg, 1 mmol) in 20 ml water was stirred for 10 min at room temperature, then the Cu(OH)₂ solid was filtered. p-HMB (152.0 mg, 1 mmol) was added to the Cu(OH)₂ suspension in water with constant stirring for 1 h and a blue precipitate was obtained. It was filtered off and washed with water. Then BIE (103.1 mg, 0.5 mmol) was added to the precipitatie with stirring for 1 h and a blue solution was obtained. Blue crystals of (I) were obtained by evaporation of the solution at room temperature.

S3. Refinement

All H atoms attached to C were positioned geometrically and refined in the riding aproximation, with C–H = 0.93 Å and U_iso(H) = 1.2Ueq(C). The methyl groups were allowed to rotate but not to tip. The disordered C atoms of the BIE ligand were refined using isotropic C atoms split over two sites, with half occupancy each, and their hydrogen atoms not included in the model.

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. Ellipsoid plot of (I), drawn at the 30% probability level, showing the local coordination environment of Cu^II (Hydrogen atoms are omitted for clarity). Symmetry codes: (i) -x, -y, -z + 1; (ii) -x, y, -z + 3/2; (iii) x, -y, z - 1/2.
	Fig. 2. View of the infinite zigzag polymeric chain of (I) along the c axis.

catena-Poly[[bis(4-methoxybenzoato)copper(II)]-µ-1,1'-˘oxydiethylene)diimidazole-κ²N³:N^3']

Crystal data

[Cu(C7H4O3)2(C10H14N4O)]	F(000) = 1188
Mr = 572.06	Dx = 1.484 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 8430 reflections
a = 21.866 (13) Å	θ = 3.0–24.4°
b = 7.699 (4) Å	µ = 0.91 mm^−1
c = 15.519 (8) Å	T = 293 K
β = 101.44 (2)°	Plate, blue
V = 2561 (2) Å^3	0.49 × 0.48 × 0.06 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	2899 independent reflections
Radiation source: rotor target	2106 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 10.0 pixels mm^-1	θmax = 27.4°, θmin = 3.0°
ω scans	h = −28→28
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −9→9
Tmin = 0.65, Tmax = 0.950	l = −20→20
11978 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0869P)^2 + 1.4878P] where P = (Fo^2 + 2Fc^2)/3
2899 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.49 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	0.0000	0.0000	0.5000	0.0411 (2)
C1	0.03679 (17)	0.3163 (5)	0.6067 (3)	0.0674 (10)
H1	0.0143	0.2802	0.6484	0.081*
C2	0.07700 (18)	0.3296 (5)	0.4927 (2)	0.0638 (9)
H2	0.0878	0.3015	0.4393	0.077*
C3	0.0962 (2)	0.4710 (5)	0.5402 (3)	0.0743 (12)
H3	0.1217	0.5587	0.5261	0.089*
C4	0.0739 (5)	0.6360 (11)	0.6582 (7)	0.073 (2)	0.50
C4'	0.0884 (5)	0.5482 (14)	0.7085 (6)	0.066 (2)	0.50
C5	0.0754 (5)	0.5791 (16)	0.7487 (7)	0.076 (3)	0.50
C5'	0.0296 (5)	0.6503 (10)	0.7251 (5)	0.0632 (19)	0.50
C6	−0.09631 (15)	0.0740 (4)	0.5710 (2)	0.0451 (7)
C7	−0.13921 (14)	0.0973 (4)	0.63396 (19)	0.0438 (7)
C8	−0.19905 (16)	0.1591 (6)	0.6029 (2)	0.0641 (10)
H8	−0.2118	0.1832	0.5433	0.077*
C9	−0.23998 (16)	0.1856 (6)	0.6589 (2)	0.0689 (11)
H9	−0.2798	0.2283	0.6370	0.083*
C10	−0.22173 (15)	0.1485 (5)	0.7478 (2)	0.0539 (8)
C11	−0.16211 (16)	0.0878 (5)	0.7807 (2)	0.0535 (8)
H11	−0.1494	0.0636	0.8403	0.064*
C12	−0.12126 (15)	0.0635 (5)	0.7230 (2)	0.0488 (7)
H12	−0.0810	0.0236	0.7449	0.059*
C13	−0.2490 (2)	0.1688 (7)	0.8892 (3)	0.0852 (14)
H13A	−0.2851	0.1888	0.9144	0.128*
H13B	−0.2184	0.2568	0.9091	0.128*
H13C	−0.2318	0.0567	0.9071	0.128*
N1	0.03890 (11)	0.2319 (3)	0.53434 (16)	0.0475 (6)
N2	0.07111 (15)	0.4613 (5)	0.6132 (3)	0.0815 (12)
O1	−0.26625 (11)	0.1746 (4)	0.79675 (16)	0.0749 (8)
O2	−0.11383 (11)	0.1160 (3)	0.49215 (14)	0.0567 (6)
O3	−0.04254 (10)	0.0090 (3)	0.60132 (15)	0.0479 (5)
O4	0.0158 (2)	0.5193 (6)	0.7619 (6)	0.0626 (18)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0408 (3)	0.0455 (3)	0.0388 (3)	0.0011 (2)	0.0126 (2)	−0.0031 (2)
C1	0.051 (2)	0.078 (3)	0.079 (2)	−0.0133 (19)	0.0260 (17)	−0.036 (2)
C2	0.074 (2)	0.061 (2)	0.0566 (19)	−0.0173 (19)	0.0136 (17)	0.0050 (18)
C3	0.065 (3)	0.057 (2)	0.097 (3)	−0.0103 (18)	0.006 (2)	−0.003 (2)
C4	0.101 (7)	0.059 (5)	0.069 (5)	−0.019 (5)	0.037 (5)	−0.023 (4)
C4'	0.081 (6)	0.077 (6)	0.039 (4)	−0.022 (5)	0.007 (4)	−0.015 (5)
C5	0.077 (6)	0.098 (8)	0.055 (5)	−0.037 (6)	0.018 (5)	−0.018 (6)
C5'	0.087 (6)	0.055 (5)	0.051 (4)	0.008 (4)	0.019 (4)	−0.006 (3)
C6	0.0496 (18)	0.0423 (16)	0.0457 (16)	−0.0027 (14)	0.0146 (13)	−0.0032 (14)
C7	0.0413 (16)	0.0480 (18)	0.0442 (15)	0.0001 (13)	0.0132 (12)	−0.0008 (13)
C8	0.0505 (19)	0.095 (3)	0.0467 (17)	0.0130 (19)	0.0089 (14)	0.0061 (18)
C9	0.0415 (18)	0.104 (3)	0.061 (2)	0.0192 (19)	0.0102 (15)	0.004 (2)
C10	0.0453 (17)	0.066 (2)	0.0545 (17)	0.0018 (15)	0.0206 (14)	−0.0035 (16)
C11	0.0517 (18)	0.067 (2)	0.0437 (16)	0.0055 (16)	0.0139 (13)	0.0009 (16)
C12	0.0420 (16)	0.0594 (18)	0.0455 (16)	0.0054 (14)	0.0100 (13)	0.0014 (15)
C13	0.083 (3)	0.119 (4)	0.063 (2)	0.004 (3)	0.037 (2)	−0.010 (2)
N1	0.0432 (14)	0.0485 (14)	0.0510 (14)	0.0023 (11)	0.0098 (11)	−0.0034 (12)
N2	0.0501 (18)	0.079 (2)	0.120 (3)	−0.0167 (16)	0.027 (2)	−0.057 (2)
O1	0.0518 (14)	0.114 (2)	0.0656 (15)	0.0114 (15)	0.0276 (12)	−0.0026 (15)
O2	0.0643 (14)	0.0632 (15)	0.0444 (12)	0.0041 (12)	0.0154 (10)	0.0031 (11)
O3	0.0445 (12)	0.0568 (14)	0.0446 (11)	0.0027 (10)	0.0140 (9)	−0.0034 (9)
O4	0.066 (5)	0.070 (3)	0.057 (5)	−0.001 (2)	0.025 (4)	−0.007 (3)

Geometric parameters (Å, º)

Cu1—O3	1.980 (2)	C5'—O4^ii	1.457 (10)
Cu1—O3^i	1.980 (2)	C5'—C5'^ii	1.637 (17)
Cu1—N1	2.003 (3)	C6—O2	1.249 (4)
Cu1—N1^i	2.003 (3)	C6—O3	1.279 (4)
C1—N1	1.306 (4)	C6—C7	1.494 (4)
C1—N2	1.338 (5)	C7—C12	1.384 (4)
C1—H1	0.9300	C7—C8	1.386 (5)
C2—C3	1.335 (5)	C8—C9	1.380 (5)
C2—N1	1.376 (4)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.388 (5)
C3—N2	1.354 (6)	C9—H9	0.9300
C3—H3	0.9300	C10—O1	1.363 (4)
C4—C4'	1.034 (12)	C10—C11	1.383 (5)
C4—C5	1.466 (13)	C11—C12	1.397 (4)
C4—N2	1.511 (8)	C11—H11	0.9300
C4—C5'	1.557 (11)	C12—H12	0.9300
C4'—C5	0.773 (10)	C13—O1	1.410 (4)
C4'—C5'	1.570 (14)	C13—H13A	0.9600
C4'—N2	1.599 (9)	C13—H13B	0.9600
C5—C5'	1.136 (13)	C13—H13C	0.9600
C5—O4	1.435 (11)	O4—O4^ii	0.715 (10)
C5'—O4	1.227 (10)	O4—C5'^ii	1.457 (10)
O3—Cu1—O3^i	180.0	O3—C6—C7	117.2 (3)
O3—Cu1—N1	89.95 (10)	C12—C7—C8	118.3 (3)
O3^i—Cu1—N1	90.05 (10)	C12—C7—C6	122.7 (3)
O3—Cu1—N1^i	90.05 (10)	C8—C7—C6	119.0 (3)
O3^i—Cu1—N1^i	89.95 (10)	C9—C8—C7	121.1 (3)
N1—Cu1—N1^i	180.00 (13)	C9—C8—H8	119.4
N1—C1—N2	111.4 (3)	C7—C8—H8	119.4
N1—C1—H1	124.3	C8—C9—C10	120.1 (3)
N2—C1—H1	124.3	C8—C9—H9	120.0
C3—C2—N1	109.9 (4)	C10—C9—H9	120.0
C3—C2—H2	125.1	O1—C10—C11	124.7 (3)
N1—C2—H2	125.1	O1—C10—C9	115.3 (3)
C2—C3—N2	106.4 (4)	C11—C10—C9	120.0 (3)
C2—C3—H3	126.8	C10—C11—C12	119.0 (3)
N2—C3—H3	126.8	C10—C11—H11	120.5
C4'—C4—N2	75.3 (8)	C12—C11—H11	120.5
C5—C4—N2	99.7 (8)	C7—C12—C11	121.6 (3)
N2—C4—C5'	113.5 (6)	C7—C12—H12	119.2
C5—C4'—C4	107.5 (18)	C11—C12—H12	119.2
C4—C4'—C5'	70.0 (9)	O1—C13—H13A	109.5
C5—C4'—N2	144.9 (14)	O1—C13—H13B	109.5
C4—C4'—N2	66.0 (6)	H13A—C13—H13B	109.5
C5'—C4'—N2	108.0 (6)	O1—C13—H13C	109.5
C4'—C5—C5'	109.2 (16)	H13A—C13—H13C	109.5
C4'—C5—O4	120.5 (13)	H13B—C13—H13C	109.5
C5'—C5—O4	55.6 (6)	C1—N1—C2	105.0 (3)
C5'—C5—C4	72.3 (8)	C1—N1—Cu1	125.9 (2)
O4—C5—C4	112.6 (9)	C2—N1—Cu1	128.9 (2)
C5—C5'—O4	74.7 (8)	C1—N2—C3	107.3 (3)
C5—C5'—O4^ii	101.6 (8)	C1—N2—C4	138.4 (4)
C5—C5'—C4	63.7 (7)	C3—N2—C4	110.6 (5)
O4—C5'—C4	119.8 (8)	C1—N2—C4'	116.4 (5)
O4^ii—C5'—C4	125.0 (6)	C3—N2—C4'	133.6 (5)
O4—C5'—C4'	87.2 (7)	C10—O1—C13	119.1 (3)
O4^ii—C5'—C4'	106.1 (6)	C6—O3—Cu1	105.27 (19)
C5—C5'—C5'^ii	125.2 (9)	O4^ii—O4—C5'	93.5 (10)
O4—C5'—C5'^ii	59.1 (5)	O4^ii—O4—C5	137.4 (16)
O4^ii—C5'—C5'^ii	46.3 (5)	C5'—O4—C5	49.8 (6)
C4—C5'—C5'^ii	166.1 (10)	O4^ii—O4—C5'^ii	57.2 (8)
C4'—C5'—C5'^ii	145.9 (6)	C5'—O4—C5'^ii	74.6 (7)
O2—C6—O3	122.9 (3)	C5—O4—C5'^ii	117.5 (8)
O2—C6—C7	119.9 (3)
N1—C2—C3—N2	1.1 (5)	C7—C8—C9—C10	−0.7 (7)
N2—C4—C4'—C5	−143.0 (14)	C8—C9—C10—O1	−178.3 (4)
C5'—C4—C4'—C5	−21.5 (12)	C8—C9—C10—C11	1.1 (6)
C5—C4—C4'—C5'	21.5 (12)	O1—C10—C11—C12	178.8 (3)
N2—C4—C4'—C5'	−121.5 (6)	C9—C10—C11—C12	−0.6 (6)
C5—C4—C4'—N2	143.0 (14)	C8—C7—C12—C11	0.9 (5)
C5'—C4—C4'—N2	121.5 (6)	C6—C7—C12—C11	179.4 (3)
C4—C4'—C5—C5'	30.3 (17)	C10—C11—C12—C7	−0.5 (5)
N2—C4'—C5—C5'	−43 (3)	N2—C1—N1—C2	0.1 (4)
C4—C4'—C5—O4	90.9 (17)	N2—C1—N1—Cu1	175.4 (3)
C5'—C4'—C5—O4	60.7 (12)	C3—C2—N1—C1	−0.7 (4)
N2—C4'—C5—O4	18 (4)	C3—C2—N1—Cu1	−175.9 (3)
C5'—C4'—C5—C4	−30.3 (17)	O3—Cu1—N1—C1	8.2 (3)
N2—C4'—C5—C4	−73 (3)	O3^i—Cu1—N1—C1	−171.8 (3)
N2—C4—C5—C4'	36.2 (13)	O3—Cu1—N1—C2	−177.6 (3)
C5'—C4—C5—C4'	150.0 (17)	O3^i—Cu1—N1—C2	2.4 (3)
C4'—C4—C5—C5'	−150.0 (17)	N1—C1—N2—C3	0.6 (5)
N2—C4—C5—C5'	−113.8 (8)	N1—C1—N2—C4	155.5 (8)
C4'—C4—C5—O4	−111.0 (17)	N1—C1—N2—C4'	−163.3 (5)
N2—C4—C5—O4	−74.8 (10)	C2—C3—N2—C1	−1.0 (5)
C5'—C4—C5—O4	39.1 (7)	C2—C3—N2—C4	−163.5 (5)
C4'—C5—C5'—O4	114.3 (15)	C2—C3—N2—C4'	159.0 (7)
C4—C5—C5'—O4	135.2 (7)	C4'—C4—N2—C1	70.4 (12)
C4'—C5—C5'—O4^ii	102.7 (15)	C5—C4—N2—C1	52.5 (12)
O4—C5—C5'—O4^ii	−11.7 (8)	C5'—C4—N2—C1	8.7 (14)
C4—C5—C5'—O4^ii	123.5 (7)	C4'—C4—N2—C3	−135.2 (8)
C4'—C5—C5'—C4	−20.8 (13)	C5—C4—N2—C3	−153.1 (6)
O4—C5—C5'—C4	−135.2 (7)	C5'—C4—N2—C3	163.1 (7)
O4—C5—C5'—C4'	−114.3 (15)	C5—C4—N2—C4'	−17.9 (8)
C4—C5—C5'—C4'	20.8 (13)	C5'—C4—N2—C4'	−61.7 (8)
C4'—C5—C5'—C5'^ii	146.7 (13)	C5—C4'—N2—C1	−49 (3)
O4—C5—C5'—C5'^ii	32.4 (8)	C4—C4'—N2—C1	−135.7 (7)
C4—C5—C5'—C5'^ii	167.6 (9)	C5'—C4'—N2—C1	−78.3 (8)
C4'—C4—C5'—C5	15.4 (9)	C5—C4'—N2—C3	152 (3)
N2—C4—C5'—C5	79.4 (11)	C4—C4'—N2—C3	65.7 (11)
C4'—C4—C5'—O4	−36.2 (10)	C5'—C4'—N2—C3	123.1 (7)
C5—C4—C5'—O4	−51.6 (9)	C5—C4'—N2—C4	87 (3)
N2—C4—C5'—O4	27.8 (14)	C5'—C4'—N2—C4	57.4 (8)
C4'—C4—C5'—O4^ii	−70.5 (10)	C11—C10—O1—C13	11.3 (6)
C5—C4—C5'—O4^ii	−85.9 (10)	C9—C10—O1—C13	−169.4 (4)
N2—C4—C5'—O4^ii	−6.5 (14)	O2—C6—O3—Cu1	1.0 (4)
C5—C4—C5'—C4'	−15.4 (9)	C7—C6—O3—Cu1	−179.7 (2)
N2—C4—C5'—C4'	64.0 (8)	N1—Cu1—O3—C6	93.6 (2)
C4'—C4—C5'—C5'^ii	−118 (2)	N1^i—Cu1—O3—C6	−86.4 (2)
C5—C4—C5'—C5'^ii	−133 (2)	C5—C5'—O4—O4^ii	−156.1 (15)
N2—C4—C5'—C5'^ii	−54 (3)	C4—C5'—O4—O4^ii	−109.4 (14)
C4—C4'—C5'—C5	−149.3 (19)	C4'—C5'—O4—O4^ii	−131.0 (13)
N2—C4'—C5'—C5	155.7 (19)	C5'^ii—C5'—O4—O4^ii	54.6 (12)
C5—C4'—C5'—O4	−61.6 (15)	O4^ii—C5'—O4—C5	156.1 (15)
C4—C4'—C5'—O4	149.1 (9)	C4—C5'—O4—C5	46.7 (8)
N2—C4'—C5'—O4	94.1 (8)	C4'—C5'—O4—C5	25.1 (6)
C5—C4'—C5'—O4^ii	−84.2 (16)	C5'^ii—C5'—O4—C5	−149.3 (10)
C4—C4'—C5'—O4^ii	126.5 (9)	C5—C5'—O4—C5'^ii	149.3 (10)
N2—C4'—C5'—O4^ii	71.5 (8)	O4^ii—C5'—O4—C5'^ii	−54.6 (12)
C5—C4'—C5'—C4	149.3 (19)	C4—C5'—O4—C5'^ii	−163.9 (12)
N2—C4'—C5'—C4	−55.0 (6)	C4'—C5'—O4—C5'^ii	174.4 (8)
C5—C4'—C5'—C5'^ii	−53 (2)	C4'—C5—O4—O4^ii	−57 (3)
C4—C4'—C5'—C5'^ii	157.7 (16)	C5'—C5—O4—O4^ii	36.7 (14)
N2—C4'—C5'—C5'^ii	102.7 (16)	C4—C5—O4—O4^ii	−10.0 (18)
O2—C6—C7—C12	−175.9 (3)	C4'—C5—O4—C5'	−93.4 (19)
O3—C6—C7—C12	4.8 (5)	C4—C5—O4—C5'	−46.7 (8)
O2—C6—C7—C8	2.6 (5)	C4'—C5—O4—C5'^ii	−127.1 (19)
O3—C6—C7—C8	−176.8 (3)	C5'—C5—O4—C5'^ii	−33.7 (10)
C12—C7—C8—C9	−0.4 (6)	C4—C5—O4—C5'^ii	−80.3 (12)
C6—C7—C8—C9	−178.9 (4)

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