Crystal structure of tetra­kis­[μ-2-(meth­oxy­carbon­yl)benzoato-κ²O¹:O^1′]bis­[(N,N-di­methyl­formamide-κO)copper(II)](Cu—Cu) di­methyl­formamide disolvate

The binuclear Cu^II complex displays a paddle-wheel structure. In the crystal, adjacent DMF mol­ecules coordinated to copper atoms are arranged in a mutual `head-to-tail' manner by offset face-to-face π–π stacking inter­actions, resulting in chains along the c-axis direction. These are assembled into a three-dimensional structure by further weak C—H...O and C—H...π inter­actions involving the DMF solvent mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.012 Å
• Disorder in main residue
• R factor = 0.061
• wR factor = 0.221
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N1 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         N2 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C2       -C7              1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C11      -C16             1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01167 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23A     ..O6               2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..O10              2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..O10              2.69 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...    -14.185 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.047 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.596          4 Report
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on       Cu1       1.01 eA-3

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          2 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        13% Note
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C20 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C21 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C23 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C24 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         12 Note
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
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Tetrakis[µ-2-(methoxycarbonyl)benzoato-κ²O¹:O^1']bis[(N,N-dimethylformamide-κO)copper(II)](Cu—Cu) dimethylformamide disolvate

Crystal data

[Cu2(C9H7O4)4(C3H7NO)2]·2C3H7NO	F(000) = 1180
Mr = 1136.07	Dx = 1.447 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7775 (12) Å	Cell parameters from 2608 reflections
b = 19.746 (2) Å	θ = 2.2–21.7°
c = 10.7957 (11) Å	µ = 0.90 mm^−1
β = 106.870 (2)°	T = 296 K
V = 2606.6 (4) Å^3	Block, blue
Z = 2	0.45 × 0.34 × 0.21 mm

Data collection

Bruker Photon 100 diffractometer	2522 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.101
φ and ω scans	θmax = 25.1°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −12→15
Tmin = 0.689, Tmax = 0.834	k = −23→17
12822 measured reflections	l = −12→12
4610 independent reflections

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.221	w = 1/[σ^2(Fo^2) + (0.1098P)^2 + 2.5593P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4610 reflections	Δρmax = 0.91 e Å^−3
373 parameters	Δρmin = −0.54 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.51748 (6)	0.48436 (4)	0.62288 (7)	0.0317 (3)
N1	0.4576 (5)	0.4167 (3)	0.9654 (5)	0.0451 (14)
N2	0.0957 (5)	0.9334 (4)	0.6092 (6)	0.0641 (19)
O1	0.4075 (4)	0.4160 (2)	0.5502 (4)	0.0439 (12)
O2	0.3789 (3)	0.4416 (2)	0.3420 (4)	0.0447 (12)
O5	0.4004 (3)	0.5502 (2)	0.6162 (4)	0.0413 (11)
O6	0.3716 (3)	0.5759 (2)	0.4083 (4)	0.0431 (12)
O7	0.1773 (7)	0.5501 (4)	0.7540 (7)	0.116 (3)
O8	0.1653 (4)	0.5121 (3)	0.5590 (6)	0.0668 (16)
O9	0.5355 (3)	0.4523 (2)	0.8165 (4)	0.0409 (11)
O10	−0.0745 (6)	0.8955 (4)	0.5178 (7)	0.110 (3)
C1	0.3623 (5)	0.4065 (3)	0.4326 (7)	0.0363 (16)
C2	0.2811 (5)	0.3508 (3)	0.3972 (6)	0.0341 (15)
C3	0.2052 (5)	0.3496 (4)	0.2792 (7)	0.0472 (18)
H3	0.206712	0.382714	0.218399	0.057*
C4	0.1263 (6)	0.3001 (4)	0.2487 (7)	0.053 (2)
H4	0.074745	0.300086	0.167725	0.064*
C5	0.1230 (6)	0.2512 (4)	0.3359 (8)	0.056 (2)
H5	0.069538	0.217744	0.314463	0.067*
C6	0.1986 (6)	0.2512 (4)	0.4554 (8)	0.0530 (19)
H6	0.196603	0.217854	0.515469	0.064*
C7	0.2772 (6)	0.3005 (4)	0.4863 (7)	0.0476 (18)
C8	0.3466 (11)	0.3011 (6)	0.6261 (14)	0.048 (3)	0.751 (12)
O3	0.3230 (6)	0.3196 (4)	0.7184 (7)	0.064 (3)	0.751 (12)
O4	0.4429 (10)	0.2714 (6)	0.6315 (11)	0.060 (3)	0.751 (12)
C9	0.5209 (13)	0.2647 (9)	0.7578 (13)	0.097 (6)	0.751 (12)
H9A	0.535773	0.308469	0.797628	0.145*	0.751 (12)
H9B	0.587480	0.245487	0.749156	0.145*	0.751 (12)
H9C	0.491382	0.235598	0.810555	0.145*	0.751 (12)
C8A	0.391 (4)	0.283 (2)	0.580 (5)	0.052 (12)	0.249 (12)
O3A	0.4754 (18)	0.2744 (13)	0.561 (3)	0.064 (8)	0.249 (12)
O4A	0.370 (2)	0.2762 (16)	0.688 (3)	0.060 (4)	0.249 (12)
C9A	0.470 (4)	0.259 (3)	0.798 (5)	0.096 (6)	0.249 (12)
H9A1	0.480823	0.211297	0.802431	0.144*	0.249 (12)
H9A2	0.459759	0.275219	0.877950	0.144*	0.249 (12)
H9A3	0.532924	0.281117	0.784324	0.144*	0.249 (12)
C10	0.3532 (5)	0.5818 (3)	0.5149 (6)	0.0356 (15)
C11	0.2753 (5)	0.6360 (4)	0.5253 (7)	0.0441 (17)
C12	0.2796 (7)	0.6975 (4)	0.4697 (8)	0.064 (2)
H12	0.328128	0.704014	0.421111	0.077*
C13	0.2133 (8)	0.7503 (5)	0.4842 (10)	0.085 (3)
H13	0.217287	0.792384	0.447102	0.102*
C14	0.1418 (9)	0.7390 (6)	0.5547 (11)	0.094 (3)
H14	0.095559	0.773774	0.564212	0.113*
C15	0.1368 (7)	0.6792 (6)	0.6101 (9)	0.079 (3)
H15	0.088721	0.673494	0.659549	0.095*
C16	0.2008 (6)	0.6260 (4)	0.5959 (7)	0.052 (2)
C17	0.1818 (6)	0.5593 (5)	0.6481 (9)	0.064 (2)
C18	0.1415 (8)	0.4457 (5)	0.5937 (11)	0.095 (3)
H18A	0.131302	0.416073	0.520669	0.143*
H18B	0.201215	0.429533	0.663889	0.143*
H18C	0.076007	0.446603	0.620192	0.143*
C19	0.4544 (6)	0.4433 (4)	0.8545 (6)	0.0433 (17)
H19	0.386642	0.456500	0.800306	0.052*
C20	0.5587 (7)	0.3926 (4)	1.0530 (8)	0.072 (3)
H20A	0.544984	0.374755	1.129558	0.107*
H20B	0.588580	0.357686	1.011590	0.107*
H20C	0.609754	0.429424	1.076264	0.107*
C21	0.3581 (7)	0.4049 (5)	1.0006 (9)	0.078 (3)
H21A	0.375788	0.385056	1.085330	0.117*
H21B	0.320836	0.447112	1.000652	0.117*
H21C	0.311570	0.374657	0.939037	0.117*
C22	0.0126 (9)	0.9123 (5)	0.5152 (10)	0.089 (3)
H22	0.024510	0.910232	0.434322	0.107*
C23	0.1986 (7)	0.9484 (6)	0.5900 (10)	0.105 (4)
H23A	0.248667	0.963075	0.670171	0.157*
H23B	0.226912	0.908478	0.560193	0.157*
H23C	0.189853	0.983615	0.526528	0.157*
C24	0.0870 (9)	0.9415 (9)	0.7348 (11)	0.149 (6)
H24A	0.155395	0.957274	0.790841	0.223*
H24B	0.030640	0.973821	0.733691	0.223*
H24C	0.068855	0.898752	0.765799	0.223*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0357 (4)	0.0410 (5)	0.0215 (4)	0.0001 (4)	0.0133 (3)	0.0025 (4)
N1	0.069 (4)	0.044 (4)	0.030 (3)	−0.013 (3)	0.027 (3)	−0.006 (3)
N2	0.051 (4)	0.086 (5)	0.050 (4)	−0.012 (4)	0.007 (3)	0.002 (4)
O1	0.050 (3)	0.054 (3)	0.028 (3)	−0.010 (2)	0.012 (2)	0.000 (2)
O2	0.047 (3)	0.056 (3)	0.031 (3)	−0.012 (2)	0.013 (2)	0.005 (2)
O5	0.045 (3)	0.054 (3)	0.028 (3)	0.009 (2)	0.016 (2)	0.003 (2)
O6	0.046 (3)	0.055 (3)	0.032 (3)	0.011 (2)	0.017 (2)	0.002 (2)
O7	0.155 (7)	0.145 (7)	0.075 (5)	0.000 (6)	0.077 (5)	0.017 (5)
O8	0.067 (4)	0.069 (4)	0.075 (4)	−0.006 (3)	0.038 (3)	0.003 (3)
O9	0.041 (2)	0.059 (3)	0.026 (2)	0.001 (2)	0.015 (2)	0.005 (2)
O10	0.072 (4)	0.133 (7)	0.115 (6)	−0.044 (5)	0.013 (4)	0.008 (5)
C1	0.031 (3)	0.039 (4)	0.040 (4)	−0.001 (3)	0.012 (3)	−0.002 (3)
C2	0.036 (3)	0.037 (4)	0.034 (4)	−0.007 (3)	0.016 (3)	0.000 (3)
C3	0.045 (4)	0.056 (5)	0.041 (5)	−0.007 (4)	0.014 (3)	0.005 (4)
C4	0.049 (4)	0.064 (5)	0.044 (5)	−0.012 (4)	0.008 (4)	−0.005 (4)
C5	0.045 (4)	0.064 (6)	0.064 (6)	−0.016 (4)	0.024 (4)	−0.013 (4)
C6	0.055 (5)	0.054 (5)	0.053 (5)	−0.007 (4)	0.020 (4)	0.004 (4)
C7	0.046 (4)	0.049 (5)	0.047 (5)	−0.009 (4)	0.011 (3)	−0.002 (4)
C8	0.058 (8)	0.038 (7)	0.050 (9)	−0.008 (5)	0.019 (7)	0.006 (6)
O3	0.088 (6)	0.070 (6)	0.048 (5)	−0.007 (4)	0.040 (4)	−0.008 (4)
O4	0.072 (7)	0.065 (6)	0.036 (6)	0.017 (5)	0.001 (5)	−0.004 (5)
C9	0.101 (13)	0.122 (11)	0.049 (9)	0.060 (11)	−0.008 (7)	−0.016 (8)
C8A	0.08 (4)	0.03 (2)	0.05 (3)	0.02 (2)	0.03 (3)	0.00 (2)
O3A	0.043 (15)	0.10 (2)	0.045 (17)	0.011 (12)	0.013 (12)	−0.008 (14)
O4A	0.070 (9)	0.064 (7)	0.035 (7)	0.010 (7)	0.000 (6)	−0.001 (6)
C9A	0.101 (13)	0.122 (11)	0.048 (9)	0.060 (11)	−0.007 (7)	−0.016 (8)
C10	0.028 (3)	0.048 (4)	0.031 (4)	−0.001 (3)	0.008 (3)	−0.003 (3)
C11	0.044 (4)	0.054 (5)	0.034 (4)	0.009 (3)	0.012 (3)	−0.004 (3)
C12	0.064 (5)	0.071 (6)	0.064 (6)	0.008 (5)	0.030 (4)	0.008 (5)
C13	0.097 (7)	0.059 (6)	0.103 (8)	0.028 (6)	0.034 (7)	0.008 (6)
C14	0.101 (8)	0.098 (9)	0.092 (8)	0.050 (7)	0.040 (7)	0.001 (7)
C15	0.073 (6)	0.104 (8)	0.073 (7)	0.032 (6)	0.043 (5)	0.008 (6)
C16	0.046 (4)	0.073 (6)	0.040 (4)	0.019 (4)	0.018 (4)	−0.001 (4)
C17	0.044 (4)	0.105 (8)	0.052 (5)	0.012 (5)	0.028 (4)	0.007 (5)
C18	0.080 (7)	0.088 (8)	0.139 (10)	0.001 (6)	0.067 (7)	0.012 (7)
C19	0.047 (4)	0.053 (5)	0.033 (4)	0.000 (3)	0.016 (3)	−0.004 (3)
C20	0.096 (6)	0.086 (7)	0.040 (5)	0.016 (5)	0.030 (5)	0.025 (5)
C21	0.103 (7)	0.079 (6)	0.077 (6)	−0.021 (5)	0.065 (6)	−0.008 (5)
C22	0.091 (8)	0.075 (7)	0.085 (8)	−0.003 (6)	0.000 (7)	−0.004 (6)
C23	0.066 (6)	0.158 (11)	0.100 (8)	−0.007 (7)	0.039 (6)	−0.022 (8)
C24	0.097 (8)	0.29 (2)	0.067 (8)	−0.016 (10)	0.040 (7)	−0.015 (10)

Geometric parameters (Å, º)

Cu1—Cu1^i	2.6329 (14)	C9—H9B	0.9600
Cu1—O1	1.943 (4)	C9—H9C	0.9600
Cu1—O2^i	1.934 (4)	C8A—O3A	1.17 (5)
Cu1—O5	1.968 (4)	C8A—O4A	1.28 (6)
Cu1—O6^i	1.953 (4)	O4A—C9A	1.50 (5)
Cu1—O9	2.132 (4)	C9A—H9A1	0.9600
N1—C19	1.297 (8)	C9A—H9A2	0.9600
N1—C20	1.442 (10)	C9A—H9A3	0.9600
N1—C21	1.448 (9)	C10—C11	1.488 (9)
N2—C22	1.306 (10)	C11—C12	1.363 (10)
N2—C24	1.401 (11)	C11—C16	1.395 (9)
N2—C23	1.421 (10)	C12—C13	1.381 (11)
O1—C1	1.247 (7)	C12—H12	0.9300
O2—C1	1.266 (7)	C13—C14	1.367 (13)
O5—C10	1.251 (7)	C13—H13	0.9300
O6—C10	1.245 (7)	C14—C15	1.335 (13)
O7—C17	1.176 (9)	C14—H14	0.9300
O8—C17	1.313 (10)	C15—C16	1.366 (11)
O8—C18	1.420 (10)	C15—H15	0.9300
O9—C19	1.234 (7)	C16—C17	1.480 (12)
O10—C22	1.169 (11)	C18—H18A	0.9600
C1—C2	1.485 (9)	C18—H18B	0.9600
C2—C3	1.359 (9)	C18—H18C	0.9600
C2—C7	1.393 (9)	C19—H19	0.9300
C3—C4	1.374 (9)	C20—H20A	0.9600
C3—H3	0.9300	C20—H20B	0.9600
C4—C5	1.357 (10)	C20—H20C	0.9600
C4—H4	0.9300	C21—H21A	0.9600
C5—C6	1.370 (10)	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—C7	1.367 (9)	C22—H22	0.9300
C6—H6	0.9300	C23—H23A	0.9600
C7—C8	1.513 (16)	C23—H23B	0.9600
C7—C8A	1.55 (5)	C23—H23C	0.9600
C8—O3	1.179 (15)	C24—H24A	0.9600
C8—O4	1.349 (19)	C24—H24B	0.9600
O4—C9	1.442 (16)	C24—H24C	0.9600
C9—H9A	0.9600
O2^i—Cu1—O1	168.03 (18)	O4A—C9A—H9A2	109.5
O2^i—Cu1—O6^i	90.25 (19)	H9A1—C9A—H9A2	109.5
O1—Cu1—O6^i	89.05 (19)	O4A—C9A—H9A3	109.5
O2^i—Cu1—O5	88.7 (2)	H9A1—C9A—H9A3	109.5
O1—Cu1—O5	89.48 (19)	H9A2—C9A—H9A3	109.5
O6^i—Cu1—O5	168.06 (18)	O6—C10—O5	126.1 (6)
O2^i—Cu1—O9	99.14 (18)	O6—C10—C11	116.6 (6)
O1—Cu1—O9	92.82 (18)	O5—C10—C11	117.1 (6)
O6^i—Cu1—O9	96.36 (17)	C12—C11—C16	119.2 (7)
O5—Cu1—O9	95.55 (17)	C12—C11—C10	119.6 (6)
O2^i—Cu1—Cu1^i	85.81 (13)	C16—C11—C10	121.2 (7)
O1—Cu1—Cu1^i	82.24 (13)	C11—C12—C13	121.2 (8)
O6^i—Cu1—Cu1^i	83.61 (13)	C11—C12—H12	119.4
O5—Cu1—Cu1^i	84.46 (13)	C13—C12—H12	119.4
O9—Cu1—Cu1^i	175.05 (13)	C14—C13—C12	118.1 (9)
C19—N1—C20	121.4 (6)	C14—C13—H13	120.9
C19—N1—C21	120.8 (7)	C12—C13—H13	120.9
C20—N1—C21	117.6 (6)	C15—C14—C13	121.4 (9)
C22—N2—C24	120.9 (9)	C15—C14—H14	119.3
C22—N2—C23	122.1 (9)	C13—C14—H14	119.3
C24—N2—C23	117.1 (8)	C14—C15—C16	121.5 (8)
C1—O1—Cu1	125.6 (4)	C14—C15—H15	119.3
C1—O2—Cu1^i	121.4 (4)	C16—C15—H15	119.3
C10—O5—Cu1	122.0 (4)	C15—C16—C11	118.6 (8)
C10—O6—Cu1^i	123.9 (4)	C15—C16—C17	118.1 (7)
C17—O8—C18	117.6 (7)	C11—C16—C17	123.1 (7)
C19—O9—Cu1	120.4 (4)	O7—C17—O8	124.0 (10)
O1—C1—O2	125.0 (6)	O7—C17—C16	124.6 (10)
O1—C1—C2	117.1 (6)	O8—C17—C16	111.3 (7)
O2—C1—C2	118.0 (6)	O8—C18—H18A	109.5
C3—C2—C7	118.5 (6)	O8—C18—H18B	109.5
C3—C2—C1	120.5 (6)	H18A—C18—H18B	109.5
C7—C2—C1	120.9 (6)	O8—C18—H18C	109.5
C2—C3—C4	120.6 (7)	H18A—C18—H18C	109.5
C2—C3—H3	119.7	H18B—C18—H18C	109.5
C4—C3—H3	119.7	O9—C19—N1	124.1 (7)
C5—C4—C3	120.6 (7)	O9—C19—H19	118.0
C5—C4—H4	119.7	N1—C19—H19	118.0
C3—C4—H4	119.7	N1—C20—H20A	109.5
C4—C5—C6	119.8 (7)	N1—C20—H20B	109.5
C4—C5—H5	120.1	H20A—C20—H20B	109.5
C6—C5—H5	120.1	N1—C20—H20C	109.5
C7—C6—C5	119.8 (7)	H20A—C20—H20C	109.5
C7—C6—H6	120.1	H20B—C20—H20C	109.5
C5—C6—H6	120.1	N1—C21—H21A	109.5
C6—C7—C2	120.6 (7)	N1—C21—H21B	109.5
C6—C7—C8	115.1 (7)	H21A—C21—H21B	109.5
C2—C7—C8	123.7 (7)	N1—C21—H21C	109.5
C6—C7—C8A	119.2 (17)	H21A—C21—H21C	109.5
C2—C7—C8A	113.0 (18)	H21B—C21—H21C	109.5
O3—C8—O4	123.5 (13)	O10—C22—N2	129.6 (11)
O3—C8—C7	128.7 (13)	O10—C22—H22	115.2
O4—C8—C7	107.7 (12)	N2—C22—H22	115.2
C8—O4—C9	116.9 (13)	N2—C23—H23A	109.5
O4—C9—H9A	109.5	N2—C23—H23B	109.5
O4—C9—H9B	109.5	H23A—C23—H23B	109.5
H9A—C9—H9B	109.5	N2—C23—H23C	109.5
O4—C9—H9C	109.5	H23A—C23—H23C	109.5
H9A—C9—H9C	109.5	H23B—C23—H23C	109.5
H9B—C9—H9C	109.5	N2—C24—H24A	109.5
O3A—C8A—O4A	126 (5)	N2—C24—H24B	109.5
O3A—C8A—C7	131 (5)	H24A—C24—H24B	109.5
O4A—C8A—C7	102 (4)	N2—C24—H24C	109.5
C8A—O4A—C9A	113 (4)	H24A—C24—H24C	109.5
O4A—C9A—H9A1	109.5	H24B—C24—H24C	109.5
Cu1—O1—C1—O2	−2.2 (9)	O3A—C8A—O4A—C9A	5 (6)
Cu1—O1—C1—C2	179.2 (4)	C7—C8A—O4A—C9A	−180 (3)
Cu1^i—O2—C1—O1	1.3 (9)	Cu1^i—O6—C10—O5	−1.1 (9)
Cu1^i—O2—C1—C2	179.8 (4)	Cu1^i—O6—C10—C11	172.8 (4)
O1—C1—C2—C3	159.7 (6)	Cu1—O5—C10—O6	0.9 (9)
O2—C1—C2—C3	−18.9 (9)	Cu1—O5—C10—C11	−173.0 (4)
O1—C1—C2—C7	−16.9 (9)	O6—C10—C11—C12	−41.0 (9)
O2—C1—C2—C7	164.5 (6)	O5—C10—C11—C12	133.5 (7)
C7—C2—C3—C4	0.2 (10)	O6—C10—C11—C16	141.9 (7)
C1—C2—C3—C4	−176.5 (6)	O5—C10—C11—C16	−43.6 (9)
C2—C3—C4—C5	−0.3 (11)	C16—C11—C12—C13	1.3 (12)
C3—C4—C5—C6	0.2 (11)	C10—C11—C12—C13	−175.9 (8)
C4—C5—C6—C7	−0.1 (11)	C11—C12—C13—C14	−0.9 (14)
C5—C6—C7—C2	0.0 (11)	C12—C13—C14—C15	1.1 (17)
C5—C6—C7—C8	172.2 (9)	C13—C14—C15—C16	−1.9 (17)
C5—C6—C7—C8A	−148 (2)	C14—C15—C16—C11	2.2 (14)
C3—C2—C7—C6	−0.1 (10)	C14—C15—C16—C17	−173.3 (9)
C1—C2—C7—C6	176.6 (6)	C12—C11—C16—C15	−1.9 (11)
C3—C2—C7—C8	−171.6 (9)	C10—C11—C16—C15	175.2 (7)
C1—C2—C7—C8	5.1 (12)	C12—C11—C16—C17	173.4 (8)
C3—C2—C7—C8A	150.1 (19)	C10—C11—C16—C17	−9.5 (11)
C1—C2—C7—C8A	−33 (2)	C18—O8—C17—O7	−0.5 (12)
C6—C7—C8—O3	−74.5 (14)	C18—O8—C17—C16	−177.6 (6)
C2—C7—C8—O3	97.4 (13)	C15—C16—C17—O7	−51.0 (12)
C6—C7—C8—O4	101.3 (10)	C11—C16—C17—O7	133.7 (9)
C2—C7—C8—O4	−86.8 (12)	C15—C16—C17—O8	126.0 (8)
O3—C8—O4—C9	−2 (2)	C11—C16—C17—O8	−49.3 (10)
C7—C8—O4—C9	−178.1 (12)	Cu1—O9—C19—N1	171.9 (5)
C6—C7—C8A—O3A	106 (4)	C20—N1—C19—O9	−2.4 (11)
C2—C7—C8A—O3A	−45 (5)	C21—N1—C19—O9	−177.0 (7)
C6—C7—C8A—O4A	−70 (3)	C24—N2—C22—O10	−2.6 (18)
C2—C7—C8A—O4A	139 (2)	C23—N2—C22—O10	176.5 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3A^i	0.93	2.50	3.29 (3)	143
C23—H23A···O6^ii	0.96	2.70	3.538 (11)	145
C3—H3···O10^iii	0.93	2.63	3.284 (10)	128
C6—H6···O10^iv	0.93	2.69	3.355 (11)	129

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