Poly[[μ-1,3-bis­(pyridin-3-yl)urea]bis­(μ₄-glutarato)dicopper(II)]

The title compound, [Cu₂(C₅H₆O₄)₂(C₁₁H₁₀N₄O)]_n, contains square-pyramidally coordinated Cu^II ions linked by anti-gauche conformation glutarate (glu) ligands into [Cu₂(glu)₂]_n di-periodic coordination polymer layers with embedded [Cu₂(OCO)₄] paddlewheel clusters. In turn, the layer motifs are connected by 1,3-di(pyridin-3-yl)urea (3-dpu) linkers to form a [Cu₂(glu)₂(3-dpu)]_n tri-periodic coordination polymer network. Treating the [Cu₂(OCO)₄] clusters as 6-connected nodes reveals an underlying 4¹²6³ pcu topology according to TOPOSPRO software [Blatov et al. (2014). Cryst. Growth Des. 14, 3576–3586].

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.042
• wR factor = 0.109
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT112_ALERT_2_C ADDSYM Detects New (Pseudo) Symm. Elem       c/2         83 %Fit

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          3 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4       ..C17      .       2.97 Ang.
                                                1-x,1-y,1-z  =      3_666 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Cu1       (II)      .       2.08 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cu2       (II)      .       2.12 Info
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        63% Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.3 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   4 ALERT type 5 Informative message, check

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Computing details

Data collection: COSMO (Bruker, 2009); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: CrystalMaker (Palmer, 2020); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Poly[[µ-1,3-bis(pyridin-3-yl)urea]bis(µ₄-glutarato)dicopper(II)]

Crystal data

[Cu2(C5H6O4)2(C11H10N4O)]	F(000) = 1224
Mr = 601.50	Dx = 1.721 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.5042 (11) Å	Cell parameters from 5350 reflections
b = 13.3095 (17) Å	θ = 2.5–25.3°
c = 20.921 (3) Å	µ = 1.89 mm^−1
β = 101.348 (1)°	T = 173 K
V = 2321.7 (5) Å^3	Block, green
Z = 4	0.22 × 0.13 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	4229 independent reflections
Radiation source: sealed tube	3163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 8.36 pixels mm^-1	θmax = 25.3°, θmin = 1.8°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −15→16
Tmin = 0.669, Tmax = 0.745	l = −24→25
18339 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 1.6221P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4229 reflections	Δρmax = 0.72 e Å^−3
325 parameters	Δρmin = −0.60 e Å^−3
0 restraints

Special details

Experimental. Data was collected using a BRUKER CCD (charge-coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a nylon loop using Paratone oil. Data were measured using ω scans of 0.5° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software, which corrects for Lp. Scaling and absorption corrections were applied using SADABS multi-scan technique, supplied by George Sheldrick. The structure was solved by dual-space methods using the SHELXT program and refined by the least squares method on F², SHELXL, incorporated in Olex2.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structure was refined by least-squares using version 2018/3 of SHELXL (Sheldrick, 2015b) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the hydrogen atom on the nitrogen atom which was found by difference-Fourier methods and refined isotropically.

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

	x	y	z	Uiso*/Ueq
Cu1	0.51833 (5)	0.46750 (3)	0.69093 (2)	0.01968 (15)
Cu2	0.47185 (5)	0.55687 (3)	0.79894 (2)	0.01879 (15)
O1	0.2886 (3)	0.4836 (2)	0.65382 (13)	0.0266 (6)
O2	0.2499 (3)	0.55198 (19)	0.74755 (13)	0.0248 (6)
O3	0.0222 (3)	0.84023 (19)	0.76407 (14)	0.0290 (7)
O4	0.0402 (3)	0.9183 (2)	0.67157 (13)	0.0282 (7)
O5	0.9976 (3)	0.18497 (18)	0.74221 (13)	0.0266 (6)
O6	0.9526 (3)	0.11028 (19)	0.83279 (13)	0.0264 (6)
O7	0.7420 (3)	0.46407 (19)	0.73954 (12)	0.0223 (6)
O8	0.7091 (3)	0.5446 (2)	0.82984 (13)	0.0266 (7)
O9	0.7057 (4)	0.1263 (2)	0.45026 (13)	0.0437 (9)
N1	0.6018 (4)	0.4047 (2)	0.60804 (15)	0.0235 (7)
N2	0.7042 (4)	0.1563 (3)	0.55713 (15)	0.0290 (8)
H2	0.707005	0.127120	0.595097	0.035*
N3	0.7539 (4)	−0.0029 (2)	0.52353 (15)	0.0272 (8)
H3	0.752940	−0.020425	0.564012	0.033*
N4	0.8952 (4)	−0.1190 (2)	0.38504 (15)	0.0213 (7)
C1	0.2035 (4)	0.5284 (3)	0.6882 (2)	0.0222 (9)
C2	0.0334 (4)	0.5567 (3)	0.6570 (2)	0.0245 (9)
H2A	−0.039149	0.501040	0.663455	0.029*
H2B	0.026550	0.564775	0.609461	0.029*
C3	−0.0253 (5)	0.6543 (3)	0.6844 (2)	0.0267 (9)
H3A	−0.137370	0.667748	0.662406	0.032*
H3B	−0.023492	0.645728	0.731569	0.032*
C4	0.0800 (5)	0.7435 (3)	0.6744 (2)	0.0298 (10)
H4A	0.193184	0.725572	0.692056	0.036*
H4B	0.069537	0.754582	0.626932	0.036*
C5	0.0429 (4)	0.8420 (3)	0.70553 (18)	0.0198 (8)
C6	0.9644 (4)	0.1855 (3)	0.79894 (18)	0.0200 (8)
C7	0.9325 (4)	0.2872 (3)	0.82592 (19)	0.0237 (9)
H7A	0.958344	0.283487	0.874114	0.028*
H7B	0.816469	0.301817	0.812897	0.028*
C8	1.0251 (4)	0.3746 (3)	0.80450 (18)	0.0211 (8)
H8A	1.011660	0.374029	0.756416	0.025*
H8B	1.140653	0.366472	0.823249	0.025*
C9	0.9671 (4)	0.4753 (3)	0.82633 (19)	0.0204 (8)
H9A	0.979623	0.475401	0.874385	0.024*
H9B	1.034981	0.529804	0.814258	0.024*
C10	0.7939 (4)	0.4961 (3)	0.79597 (18)	0.0183 (8)
C11	0.6422 (5)	0.4641 (3)	0.56210 (19)	0.0286 (10)
H11	0.628070	0.534704	0.564579	0.034*
C12	0.7044 (5)	0.4241 (3)	0.5107 (2)	0.0368 (11)
H12	0.732802	0.467621	0.478814	0.044*
C13	0.7252 (5)	0.3215 (3)	0.5058 (2)	0.0328 (10)
H13	0.766286	0.293544	0.470630	0.039*
C14	0.6838 (5)	0.2605 (3)	0.55413 (18)	0.0240 (9)
C15	0.6222 (4)	0.3057 (3)	0.60408 (18)	0.0235 (9)
H15	0.593448	0.264071	0.636822	0.028*
C16	0.7203 (5)	0.0954 (3)	0.50550 (19)	0.0274 (9)
C17	0.8596 (4)	−0.0510 (3)	0.42751 (18)	0.0224 (9)
H17	0.882606	0.017838	0.421486	0.027*
C18	0.7902 (5)	−0.0778 (3)	0.48003 (19)	0.0239 (9)
C19	0.7588 (5)	−0.1777 (3)	0.4894 (2)	0.0353 (11)
H19	0.712509	−0.198164	0.525082	0.042*
C20	0.7964 (6)	−0.2481 (3)	0.4455 (2)	0.0405 (12)
H20	0.776981	−0.317547	0.451056	0.049*
C21	0.8624 (5)	−0.2156 (3)	0.3938 (2)	0.0323 (10)
H21	0.885280	−0.263684	0.363304	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0195 (3)	0.0170 (3)	0.0230 (3)	0.00133 (19)	0.0054 (2)	−0.00298 (19)
Cu2	0.0198 (3)	0.0156 (3)	0.0222 (3)	0.00055 (19)	0.0071 (2)	0.00043 (19)
O1	0.0186 (14)	0.0299 (16)	0.0298 (16)	0.0036 (12)	0.0014 (12)	−0.0097 (13)
O2	0.0209 (14)	0.0278 (16)	0.0263 (16)	0.0039 (12)	0.0061 (12)	0.0004 (12)
O3	0.0356 (17)	0.0153 (15)	0.0383 (18)	0.0027 (12)	0.0126 (14)	0.0039 (12)
O4	0.0403 (17)	0.0177 (15)	0.0288 (16)	0.0006 (13)	0.0123 (13)	−0.0039 (13)
O5	0.0406 (17)	0.0150 (14)	0.0268 (16)	0.0012 (12)	0.0126 (13)	−0.0037 (12)
O6	0.0357 (16)	0.0146 (15)	0.0289 (16)	−0.0016 (12)	0.0068 (13)	−0.0029 (12)
O7	0.0187 (14)	0.0276 (16)	0.0199 (14)	0.0035 (11)	0.0023 (11)	−0.0037 (12)
O8	0.0194 (14)	0.0308 (17)	0.0295 (16)	0.0049 (12)	0.0042 (12)	−0.0090 (12)
O9	0.080 (2)	0.0320 (18)	0.0171 (16)	0.0251 (17)	0.0046 (16)	0.0016 (13)
N1	0.0268 (18)	0.0211 (18)	0.0239 (18)	0.0048 (14)	0.0079 (15)	−0.0017 (14)
N2	0.044 (2)	0.027 (2)	0.0167 (17)	0.0117 (16)	0.0086 (16)	−0.0003 (14)
N3	0.042 (2)	0.0256 (19)	0.0178 (17)	0.0054 (16)	0.0148 (15)	0.0005 (15)
N4	0.0242 (17)	0.0174 (17)	0.0237 (17)	0.0003 (13)	0.0078 (14)	−0.0056 (14)
C1	0.022 (2)	0.013 (2)	0.033 (2)	−0.0033 (16)	0.0097 (18)	0.0042 (17)
C2	0.022 (2)	0.021 (2)	0.029 (2)	0.0002 (16)	0.0010 (17)	−0.0038 (17)
C3	0.022 (2)	0.024 (2)	0.034 (2)	0.0012 (17)	0.0072 (18)	−0.0019 (18)
C4	0.031 (2)	0.021 (2)	0.040 (3)	0.0023 (18)	0.014 (2)	−0.0032 (19)
C5	0.0117 (18)	0.026 (2)	0.022 (2)	−0.0026 (16)	0.0054 (16)	−0.0031 (17)
C6	0.0151 (19)	0.022 (2)	0.023 (2)	−0.0032 (16)	0.0029 (16)	−0.0012 (17)
C7	0.026 (2)	0.019 (2)	0.027 (2)	0.0011 (17)	0.0095 (18)	−0.0001 (17)
C8	0.022 (2)	0.018 (2)	0.023 (2)	0.0011 (16)	0.0047 (16)	0.0013 (16)
C9	0.019 (2)	0.017 (2)	0.025 (2)	−0.0013 (15)	0.0029 (16)	−0.0017 (16)
C10	0.023 (2)	0.0101 (18)	0.024 (2)	−0.0015 (15)	0.0094 (17)	0.0038 (16)
C11	0.035 (2)	0.024 (2)	0.026 (2)	0.0072 (18)	0.0043 (19)	0.0038 (18)
C12	0.052 (3)	0.034 (3)	0.029 (2)	0.006 (2)	0.018 (2)	0.006 (2)
C13	0.047 (3)	0.028 (2)	0.026 (2)	0.006 (2)	0.014 (2)	0.0016 (19)
C14	0.029 (2)	0.026 (2)	0.016 (2)	0.0046 (18)	0.0012 (17)	−0.0011 (17)
C15	0.026 (2)	0.027 (2)	0.019 (2)	0.0012 (17)	0.0062 (17)	0.0015 (17)
C16	0.029 (2)	0.027 (2)	0.025 (2)	0.0079 (18)	0.0035 (18)	−0.0015 (19)
C17	0.026 (2)	0.021 (2)	0.020 (2)	0.0034 (16)	0.0038 (17)	0.0002 (16)
C18	0.026 (2)	0.022 (2)	0.023 (2)	0.0048 (17)	0.0069 (17)	−0.0015 (17)
C19	0.053 (3)	0.026 (2)	0.035 (3)	−0.002 (2)	0.027 (2)	−0.0012 (19)
C20	0.068 (3)	0.019 (2)	0.042 (3)	−0.002 (2)	0.029 (3)	0.000 (2)
C21	0.047 (3)	0.025 (2)	0.030 (2)	0.004 (2)	0.019 (2)	−0.0010 (19)

Geometric parameters (Å, º)

Cu1—Cu2	2.6512 (7)	C2—C3	1.542 (5)
Cu1—O1	1.967 (3)	C3—H3A	0.9900
Cu1—O3^i	2.000 (3)	C3—H3B	0.9900
Cu1—O6^ii	1.992 (3)	C3—C4	1.527 (5)
Cu1—O7	1.973 (2)	C4—H4A	0.9900
Cu1—N1	2.167 (3)	C4—H4B	0.9900
Cu2—O2	1.981 (3)	C4—C5	1.525 (5)
Cu2—O4^i	1.954 (3)	C6—C7	1.512 (5)
Cu2—O5^ii	1.950 (3)	C7—H7A	0.9900
Cu2—O8	2.001 (3)	C7—H7B	0.9900
Cu2—N4^iii	2.194 (3)	C7—C8	1.520 (5)
O1—C1	1.266 (4)	C8—H8A	0.9900
O2—C1	1.266 (5)	C8—H8B	0.9900
O3—C5	1.271 (4)	C8—C9	1.529 (5)
O4—C5	1.236 (5)	C9—H9A	0.9900
O5—C6	1.273 (4)	C9—H9B	0.9900
O6—C6	1.242 (4)	C9—C10	1.511 (5)
O7—C10	1.251 (4)	C11—H11	0.9500
O8—C10	1.280 (4)	C11—C12	1.394 (6)
O9—C16	1.210 (5)	C12—H12	0.9500
N1—C11	1.340 (5)	C12—C13	1.383 (6)
N1—C15	1.334 (5)	C13—H13	0.9500
N2—H2	0.8800	C13—C14	1.396 (5)
N2—C14	1.398 (5)	C14—C15	1.394 (5)
N2—C16	1.378 (5)	C15—H15	0.9500
N3—H3	0.8800	C17—H17	0.9500
N3—C16	1.376 (5)	C17—C18	1.392 (5)
N3—C18	1.424 (5)	C18—C19	1.378 (6)
N4—C17	1.344 (5)	C19—H19	0.9500
N4—C21	1.336 (5)	C19—C20	1.392 (6)
C1—C2	1.513 (5)	C20—H20	0.9500
C2—H2A	0.9900	C20—C21	1.384 (6)
C2—H2B	0.9900	C21—H21	0.9500
O1—Cu1—Cu2	89.12 (8)	C3—C4—H4B	108.3
O1—Cu1—O3^i	91.61 (12)	H4A—C4—H4B	107.4
O1—Cu1—O6^ii	87.72 (11)	C5—C4—C3	115.7 (3)
O1—Cu1—O7	171.10 (11)	C5—C4—H4A	108.3
O1—Cu1—N1	100.51 (11)	C5—C4—H4B	108.3
O3^i—Cu1—Cu2	84.86 (8)	O3—C5—C4	118.4 (3)
O3^i—Cu1—N1	99.46 (12)	O4—C5—O3	125.3 (4)
O6^ii—Cu1—Cu2	80.26 (8)	O4—C5—C4	116.3 (3)
O6^ii—Cu1—O3^i	165.11 (11)	O5—C6—C7	116.2 (3)
O6^ii—Cu1—N1	95.28 (12)	O6—C6—O5	125.8 (4)
O7—Cu1—Cu2	82.03 (7)	O6—C6—C7	118.0 (3)
O7—Cu1—O3^i	88.61 (11)	C6—C7—H7A	108.4
O7—Cu1—O6^ii	89.78 (11)	C6—C7—H7B	108.4
O7—Cu1—N1	88.22 (11)	C6—C7—C8	115.7 (3)
N1—Cu1—Cu2	169.27 (9)	H7A—C7—H7B	107.4
O2—Cu2—Cu1	78.96 (8)	C8—C7—H7A	108.4
O2—Cu2—O8	164.87 (11)	C8—C7—H7B	108.4
O2—Cu2—N4^iii	93.03 (11)	C7—C8—H8A	109.3
O4^i—Cu2—Cu1	82.61 (8)	C7—C8—H8B	109.3
O4^i—Cu2—O2	92.11 (11)	C7—C8—C9	111.5 (3)
O4^i—Cu2—O8	86.16 (11)	H8A—C8—H8B	108.0
O4^i—Cu2—N4^iii	93.08 (11)	C9—C8—H8A	109.3
O5^ii—Cu2—Cu1	87.76 (8)	C9—C8—H8B	109.3
O5^ii—Cu2—O2	89.12 (11)	C8—C9—H9A	109.1
O5^ii—Cu2—O4^i	169.86 (11)	C8—C9—H9B	109.1
O5^ii—Cu2—O8	90.03 (11)	H9A—C9—H9B	107.9
O5^ii—Cu2—N4^iii	96.90 (11)	C10—C9—C8	112.3 (3)
O8—Cu2—Cu1	85.91 (8)	C10—C9—H9A	109.1
O8—Cu2—N4^iii	102.07 (11)	C10—C9—H9B	109.1
N4^iii—Cu2—Cu1	170.71 (8)	O7—C10—O8	124.2 (3)
C1—O1—Cu1	117.5 (2)	O7—C10—C9	117.9 (3)
C1—O2—Cu2	128.3 (2)	O8—C10—C9	117.9 (3)
C5—O3—Cu1^iv	120.4 (2)	N1—C11—H11	119.4
C5—O4—Cu2^iv	126.1 (3)	N1—C11—C12	121.2 (4)
C6—O5—Cu2^v	119.3 (2)	C12—C11—H11	119.4
C6—O6—Cu1^v	126.8 (3)	C11—C12—H12	119.7
C10—O7—Cu1	127.1 (2)	C13—C12—C11	120.5 (4)
C10—O8—Cu2	120.3 (2)	C13—C12—H12	119.7
C11—N1—Cu1	121.2 (3)	C12—C13—H13	121.1
C15—N1—Cu1	119.8 (3)	C12—C13—C14	117.8 (4)
C15—N1—C11	118.9 (3)	C14—C13—H13	121.1
C14—N2—H2	117.3	C13—C14—N2	124.3 (4)
C16—N2—H2	117.3	C15—C14—N2	117.2 (3)
C16—N2—C14	125.3 (3)	C15—C14—C13	118.5 (4)
C16—N3—H3	118.3	N1—C15—C14	123.1 (4)
C16—N3—C18	123.4 (3)	N1—C15—H15	118.5
C18—N3—H3	118.3	C14—C15—H15	118.5
C17—N4—Cu2^vi	115.5 (3)	O9—C16—N2	122.8 (4)
C21—N4—Cu2^vi	125.3 (3)	O9—C16—N3	124.2 (4)
C21—N4—C17	118.5 (3)	N3—C16—N2	113.0 (3)
O1—C1—C2	118.5 (3)	N4—C17—H17	118.8
O2—C1—O1	124.9 (4)	N4—C17—C18	122.3 (4)
O2—C1—C2	116.7 (3)	C18—C17—H17	118.8
C1—C2—H2A	108.8	C17—C18—N3	120.3 (4)
C1—C2—H2B	108.8	C19—C18—N3	120.8 (4)
C1—C2—C3	113.6 (3)	C19—C18—C17	118.9 (4)
H2A—C2—H2B	107.7	C18—C19—H19	120.7
C3—C2—H2A	108.8	C18—C19—C20	118.7 (4)
C3—C2—H2B	108.8	C20—C19—H19	120.7
C2—C3—H3A	109.4	C19—C20—H20	120.4
C2—C3—H3B	109.4	C21—C20—C19	119.1 (4)
H3A—C3—H3B	108.0	C21—C20—H20	120.4
C4—C3—C2	111.2 (3)	N4—C21—C20	122.4 (4)
C4—C3—H3A	109.4	N4—C21—H21	118.8
C4—C3—H3B	109.4	C20—C21—H21	118.8
C3—C4—H4A	108.3
Cu1—O1—C1—O2	−9.7 (5)	N4—C17—C18—C19	0.9 (6)
Cu1—O1—C1—C2	170.2 (2)	C1—C2—C3—C4	59.9 (5)
Cu1^iv—O3—C5—O4	−0.2 (5)	C2—C3—C4—C5	−174.3 (3)
Cu1^iv—O3—C5—C4	177.6 (2)	C3—C4—C5—O3	46.1 (5)
Cu1^v—O6—C6—O5	0.0 (5)	C3—C4—C5—O4	−135.9 (4)
Cu1^v—O6—C6—C7	178.2 (2)	C6—C7—C8—C9	171.9 (3)
Cu1—O7—C10—O8	−5.9 (5)	C7—C8—C9—C10	−62.8 (4)
Cu1—O7—C10—C9	173.4 (2)	C8—C9—C10—O7	−33.2 (5)
Cu1—N1—C11—C12	176.3 (3)	C8—C9—C10—O8	146.2 (3)
Cu1—N1—C15—C14	−176.4 (3)	C11—N1—C15—C14	0.0 (6)
Cu2—O2—C1—O1	15.3 (5)	C11—C12—C13—C14	−0.8 (7)
Cu2—O2—C1—C2	−164.6 (2)	C12—C13—C14—N2	−177.3 (4)
Cu2^iv—O4—C5—O3	7.5 (5)	C12—C13—C14—C15	0.8 (6)
Cu2^iv—O4—C5—C4	−170.3 (2)	C13—C14—C15—N1	−0.4 (6)
Cu2^v—O5—C6—O6	1.9 (5)	C14—N2—C16—O9	−6.0 (7)
Cu2^v—O5—C6—C7	−176.4 (2)	C14—N2—C16—N3	174.2 (3)
Cu2—O8—C10—O7	8.7 (5)	C15—N1—C11—C12	0.0 (6)
Cu2—O8—C10—C9	−170.6 (2)	C16—N2—C14—C13	−20.8 (6)
Cu2^vi—N4—C17—C18	171.7 (3)	C16—N2—C14—C15	161.2 (4)
Cu2^vi—N4—C21—C20	−172.1 (3)	C16—N3—C18—C17	27.5 (6)
O1—C1—C2—C3	−147.7 (3)	C16—N3—C18—C19	−153.1 (4)
O2—C1—C2—C3	32.2 (5)	C17—N4—C21—C20	−1.4 (6)
O5—C6—C7—C8	−32.1 (5)	C17—C18—C19—C20	−0.6 (6)
O6—C6—C7—C8	149.5 (3)	C18—N3—C16—O9	6.1 (6)
N1—C11—C12—C13	0.4 (7)	C18—N3—C16—N2	−174.1 (3)
N2—C14—C15—N1	177.8 (3)	C18—C19—C20—C21	−0.6 (7)
N3—C18—C19—C20	180.0 (4)	C19—C20—C21—N4	1.6 (7)
N4—C17—C18—N3	−179.7 (3)	C21—N4—C17—C18	0.1 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O8^v	0.88	1.93	2.767 (4)	157
N3—H3···O8^v	0.88	2.35	3.087 (4)	142
C13—H13···O9	0.95	2.31	2.837 (5)	115
C17—H17···O4^vii	0.95	2.33	2.973 (5)	124
C17—H17···O9	0.95	2.25	2.784 (5)	115

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