Synthesis, crystal structure and Hirshfeld surface analysis of a copper(II) complex involving 3-methyl­benzoate and 2,2′-bi­pyridine ligands

A new copper(II) complex with 3-methyl­benzoate and 2,2′-bi­pyridine synthesized displays chains of hydrogen-bonded complex units along the b axis. Hirshfeld surface analysis indicates that H...H and H...C/C...H contacts are the most important inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.042
• wR factor = 0.106
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Bond Without Acceptor  O6       --H6A      .     Please Check

Alert level C
PLAT077_ALERT_4_C Unitcell Contains Non-integer Number of Atoms ..     Please Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        O6      0.119 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         23 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         10 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         23 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         20 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT189_ALERT_3_G A Non-default SAME Restraint Value for First Par     0.0100 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0100 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        29% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       2.04 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H7       ..O6       .       2.72 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        347 Note
PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL     2019/3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         79 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

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

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: APEX2 (Bruker, 2013); data reduction: APEX2 (Bruker, 2013); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020).

Aqua(2,2'-bipyridineκ²N,N')bis(3-methylbenzoato)-κ²O,O';κO-copper(II) 0.68-hydrate,

Crystal data

[Cu(C8HH7O2)2(C10H8N2)(H2O)]·0.68H2O	F(000) = 1079
Mr = 520.26	Dx = 1.390 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.754 (3) Å	Cell parameters from 9233 reflections
b = 7.0021 (12) Å	θ = 2.5–26.6°
c = 22.103 (4) Å	µ = 0.92 mm^−1
β = 106.522 (6)°	T = 293 K
V = 2485.9 (8) Å^3	Block, blue
Z = 4	0.20 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.035
φ and ω scans	θmax = 28.5°, θmin = 2.5°
63716 measured reflections	h = −22→22
6171 independent reflections	k = −9→9
4874 reflections with I > 2σ(I)	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 1.6967P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
6171 reflections	Δρmax = 0.30 e Å^−3
418 parameters	Δρmin = −0.40 e Å^−3
347 restraints

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	0.34763 (2)	0.84495 (4)	0.31767 (2)	0.03879 (9)
O1	0.32781 (10)	0.7602 (3)	0.39681 (8)	0.0519 (4)
O2	0.26638 (14)	1.0161 (2)	0.42229 (9)	0.0664 (5)
N1	0.47164 (11)	0.8619 (2)	0.35426 (8)	0.0391 (4)
N2	0.38047 (11)	0.8817 (2)	0.23762 (8)	0.0377 (4)
C1	0.27773 (13)	0.8419 (3)	0.42213 (10)	0.0392 (4)
C2	0.23017 (13)	0.7151 (3)	0.45422 (9)	0.0372 (4)
C3	0.18273 (14)	0.7973 (3)	0.48953 (10)	0.0422 (5)
H3	0.182368	0.929463	0.493519	0.051*
C4	0.13590 (17)	0.6878 (4)	0.51900 (12)	0.0563 (6)
C5	0.1379 (2)	0.4918 (5)	0.51221 (15)	0.0735 (9)
H5	0.107167	0.415128	0.531672	0.088*
C6	0.1844 (2)	0.4077 (4)	0.47736 (17)	0.0801 (10)
H6	0.184782	0.275525	0.473485	0.096*
C7	0.23037 (18)	0.5186 (4)	0.44812 (13)	0.0571 (6)
H7	0.261503	0.461430	0.424335	0.069*
C8	0.0844 (2)	0.7820 (6)	0.55660 (18)	0.0969 (12)
H8A	0.113429	0.775074	0.600751	0.145*
H8B	0.031860	0.717351	0.548780	0.145*
H8C	0.074998	0.913325	0.544171	0.145*
O3	0.2315 (6)	0.7725 (11)	0.2675 (5)	0.0456 (16)	0.664 (4)
O4	0.2993 (4)	0.4976 (13)	0.2761 (4)	0.0443 (13)	0.664 (4)
C9	0.2338 (3)	0.5930 (10)	0.2581 (4)	0.0401 (12)	0.664 (4)
C10	0.1531 (2)	0.4981 (6)	0.2230 (2)	0.0427 (9)	0.664 (4)
C11	0.0787 (3)	0.5949 (7)	0.21325 (19)	0.0493 (9)	0.664 (4)
H11	0.079230	0.717697	0.229388	0.059*	0.664 (4)
C12	0.0028 (3)	0.5143 (9)	0.1799 (2)	0.0644 (12)	0.664 (4)
C13	0.0051 (3)	0.3318 (9)	0.1573 (3)	0.0746 (14)	0.664 (4)
H13	−0.044531	0.273815	0.135003	0.090*	0.664 (4)
C14	0.0781 (3)	0.2330 (8)	0.1666 (2)	0.0792 (13)	0.664 (4)
H14	0.077331	0.110027	0.150537	0.095*	0.664 (4)
C15	0.1529 (3)	0.3148 (7)	0.1996 (2)	0.0616 (11)	0.664 (4)
H15	0.202420	0.247440	0.206067	0.074*	0.664 (4)
C16	−0.0769 (3)	0.6241 (10)	0.1687 (3)	0.099 (2)	0.664 (4)
H16A	−0.100922	0.642619	0.124164	0.148*	0.664 (4)
H16B	−0.065780	0.745972	0.189242	0.148*	0.664 (4)
H16C	−0.115080	0.553947	0.185422	0.148*	0.664 (4)
O3'	0.2373 (12)	0.789 (2)	0.2796 (10)	0.040 (2)	0.336 (4)
O4'	0.2799 (8)	0.498 (3)	0.2621 (9)	0.047 (3)	0.336 (4)
C9'	0.2241 (6)	0.618 (2)	0.2594 (9)	0.042 (2)	0.336 (4)
C10'	0.1349 (5)	0.5677 (11)	0.2262 (4)	0.0430 (16)	0.336 (4)
C11'	0.1173 (5)	0.3862 (12)	0.2021 (4)	0.0552 (16)	0.336 (4)
H11'	0.160250	0.298071	0.207060	0.066*	0.336 (4)
C12'	0.0359 (6)	0.3330 (15)	0.1703 (6)	0.068 (2)	0.336 (4)
C13'	−0.0260 (6)	0.4669 (14)	0.1651 (5)	0.067 (2)	0.336 (4)
H13'	−0.080912	0.432829	0.145436	0.081*	0.336 (4)
C14'	−0.0089 (5)	0.6484 (14)	0.1879 (4)	0.0641 (19)	0.336 (4)
H14'	−0.051704	0.737327	0.182021	0.077*	0.336 (4)
C15'	0.0720 (4)	0.7003 (13)	0.2197 (4)	0.0503 (16)	0.336 (4)
H15'	0.083741	0.822434	0.236369	0.060*	0.336 (4)
C16'	0.0144 (7)	0.1356 (13)	0.1463 (5)	0.090 (3)	0.336 (4)
H16D	−0.002135	0.136810	0.101007	0.135*	0.336 (4)
H16E	−0.030539	0.088314	0.160979	0.135*	0.336 (4)
H16F	0.062117	0.054395	0.161428	0.135*	0.336 (4)
C17	0.51321 (16)	0.8587 (4)	0.41546 (12)	0.0524 (6)
H17	0.483401	0.844910	0.444839	0.063*
C18	0.59886 (18)	0.8753 (4)	0.43692 (14)	0.0647 (7)
H18	0.626326	0.873196	0.479876	0.078*
C19	0.64208 (17)	0.8947 (4)	0.39341 (15)	0.0650 (8)
H19	0.699777	0.905457	0.406664	0.078*
C20	0.60063 (14)	0.8983 (3)	0.33014 (13)	0.0507 (6)
H20	0.629658	0.911990	0.300250	0.061*
C21	0.51485 (13)	0.8811 (3)	0.31178 (11)	0.0369 (4)
C22	0.46312 (13)	0.8851 (3)	0.24534 (10)	0.0370 (4)
C23	0.49461 (16)	0.8923 (3)	0.19373 (12)	0.0492 (6)
H23	0.551776	0.893392	0.199385	0.059*
C24	0.4399 (2)	0.8979 (4)	0.13391 (13)	0.0593 (7)
H24	0.459856	0.901430	0.098753	0.071*
C25	0.35603 (19)	0.8982 (4)	0.12654 (12)	0.0591 (7)
H25	0.318396	0.904644	0.086519	0.071*
C26	0.32842 (16)	0.8888 (3)	0.17930 (11)	0.0501 (6)
H26	0.271393	0.887348	0.174260	0.060*
O5	0.33408 (13)	1.1632 (2)	0.33836 (11)	0.0676 (5)
H5A	0.311059	1.174260	0.367935	0.101*
H5B	0.299885	1.215072	0.306576	0.101*
O6	0.4289 (3)	0.4219 (8)	0.4465 (3)	0.119 (2)	0.680 (10)
H6A	0.441 (6)	0.309 (10)	0.446 (4)	0.178*	0.680 (10)
H6B	0.435 (6)	0.490 (13)	0.478 (4)	0.178*	0.680 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.03652 (14)	0.03638 (15)	0.04663 (16)	0.00129 (11)	0.01693 (11)	0.00307 (11)
O1	0.0532 (9)	0.0548 (10)	0.0559 (10)	0.0099 (8)	0.0286 (8)	0.0131 (8)
O2	0.1003 (15)	0.0395 (10)	0.0768 (13)	0.0003 (9)	0.0534 (12)	0.0043 (9)
N1	0.0404 (9)	0.0344 (9)	0.0418 (10)	−0.0003 (7)	0.0107 (8)	−0.0015 (7)
N2	0.0392 (9)	0.0334 (9)	0.0409 (9)	−0.0016 (7)	0.0118 (7)	0.0026 (7)
C1	0.0423 (11)	0.0412 (12)	0.0339 (10)	0.0002 (9)	0.0105 (8)	0.0004 (9)
C2	0.0405 (11)	0.0386 (11)	0.0321 (10)	−0.0017 (9)	0.0095 (8)	−0.0013 (8)
C3	0.0492 (12)	0.0418 (12)	0.0359 (11)	0.0028 (10)	0.0126 (9)	−0.0023 (9)
C4	0.0593 (15)	0.0674 (18)	0.0479 (14)	−0.0020 (13)	0.0244 (12)	−0.0018 (12)
C5	0.088 (2)	0.0661 (19)	0.080 (2)	−0.0222 (16)	0.0450 (17)	0.0024 (16)
C6	0.120 (3)	0.0390 (14)	0.097 (2)	−0.0164 (16)	0.056 (2)	−0.0061 (15)
C7	0.0755 (17)	0.0394 (13)	0.0652 (16)	−0.0015 (12)	0.0343 (14)	−0.0083 (12)
C8	0.104 (3)	0.112 (3)	0.102 (3)	0.003 (2)	0.073 (2)	−0.006 (2)
O3	0.0315 (18)	0.047 (2)	0.055 (4)	0.0020 (17)	0.007 (2)	0.005 (2)
O4	0.035 (3)	0.0400 (18)	0.057 (4)	0.002 (2)	0.011 (2)	0.006 (2)
C9	0.038 (2)	0.044 (2)	0.044 (2)	−0.006 (2)	0.0222 (19)	0.007 (2)
C10	0.0408 (19)	0.051 (2)	0.0411 (17)	−0.0051 (17)	0.0202 (15)	0.0005 (18)
C11	0.0437 (19)	0.063 (2)	0.0424 (18)	−0.005 (2)	0.0149 (15)	−0.0017 (19)
C12	0.049 (2)	0.092 (3)	0.049 (2)	−0.014 (2)	0.0094 (19)	−0.002 (2)
C13	0.066 (3)	0.096 (3)	0.058 (3)	−0.029 (3)	0.011 (2)	−0.010 (2)
C14	0.088 (3)	0.077 (3)	0.072 (3)	−0.023 (3)	0.023 (2)	−0.022 (2)
C15	0.064 (2)	0.059 (2)	0.065 (2)	−0.010 (2)	0.024 (2)	−0.0119 (19)
C16	0.041 (2)	0.159 (6)	0.085 (3)	0.001 (3)	0.000 (2)	−0.008 (4)
O3'	0.035 (4)	0.046 (4)	0.041 (5)	−0.001 (3)	0.015 (3)	−0.006 (3)
O4'	0.032 (5)	0.050 (4)	0.054 (7)	0.001 (4)	0.005 (4)	0.010 (4)
C9'	0.036 (3)	0.048 (4)	0.044 (3)	0.000 (3)	0.018 (3)	0.005 (3)
C10'	0.038 (3)	0.053 (4)	0.043 (3)	−0.007 (3)	0.020 (3)	0.000 (3)
C11'	0.051 (3)	0.065 (3)	0.053 (3)	−0.009 (3)	0.021 (3)	−0.003 (3)
C12'	0.058 (4)	0.084 (4)	0.060 (4)	−0.019 (4)	0.016 (3)	−0.005 (3)
C13'	0.054 (4)	0.089 (4)	0.055 (4)	−0.024 (4)	0.010 (3)	−0.002 (4)
C14'	0.046 (3)	0.087 (4)	0.058 (4)	−0.002 (4)	0.012 (3)	0.000 (4)
C15'	0.038 (3)	0.066 (4)	0.048 (3)	−0.002 (3)	0.014 (2)	−0.003 (3)
C16'	0.088 (6)	0.093 (7)	0.084 (6)	−0.028 (5)	0.017 (5)	−0.025 (5)
C17	0.0596 (15)	0.0513 (14)	0.0447 (13)	−0.0019 (12)	0.0123 (11)	−0.0024 (11)
C18	0.0619 (16)	0.0594 (17)	0.0576 (16)	−0.0058 (13)	−0.0075 (13)	−0.0029 (13)
C19	0.0416 (13)	0.0574 (16)	0.085 (2)	−0.0084 (12)	0.0003 (13)	0.0048 (15)
C20	0.0394 (12)	0.0397 (12)	0.0741 (17)	−0.0039 (9)	0.0179 (12)	0.0059 (11)
C21	0.0387 (10)	0.0227 (9)	0.0512 (12)	−0.0009 (8)	0.0160 (9)	0.0010 (8)
C22	0.0446 (11)	0.0198 (9)	0.0494 (12)	−0.0021 (8)	0.0177 (9)	0.0015 (8)
C23	0.0557 (14)	0.0368 (12)	0.0641 (16)	−0.0040 (10)	0.0312 (12)	−0.0008 (11)
C24	0.094 (2)	0.0431 (13)	0.0502 (15)	−0.0102 (13)	0.0362 (15)	−0.0023 (11)
C25	0.0802 (19)	0.0492 (14)	0.0423 (13)	−0.0130 (13)	0.0084 (13)	0.0026 (11)
C26	0.0501 (13)	0.0444 (13)	0.0507 (14)	−0.0057 (10)	0.0061 (11)	0.0054 (10)
O5	0.0899 (14)	0.0395 (9)	0.0894 (14)	0.0115 (9)	0.0516 (12)	0.0108 (9)
O6	0.103 (3)	0.113 (4)	0.157 (5)	0.023 (3)	0.064 (3)	0.043 (4)

Geometric parameters (Å, º)

Cu1—O3'	1.842 (17)	C16—H16A	0.9600
Cu1—O1	1.9628 (16)	C16—H16B	0.9600
Cu1—N1	2.0072 (18)	C16—H16C	0.9600
Cu1—O3	2.011 (8)	O3'—C9'	1.275 (8)
Cu1—N2	2.0131 (18)	O4'—C9'	1.248 (8)
Cu1—O5	2.2988 (18)	C9'—C10'	1.509 (7)
O1—C1	1.269 (3)	C10'—C11'	1.377 (8)
O2—C1	1.235 (3)	C10'—C15'	1.381 (8)
N1—C17	1.334 (3)	C11'—C12'	1.396 (9)
N1—C21	1.346 (3)	C11'—H11'	0.9300
N2—C26	1.336 (3)	C12'—C13'	1.378 (9)
N2—C22	1.346 (3)	C12'—C16'	1.488 (10)
C1—C2	1.499 (3)	C13'—C14'	1.367 (10)
C2—C7	1.382 (3)	C13'—H13'	0.9300
C2—C3	1.387 (3)	C14'—C15'	1.387 (8)
C3—C4	1.385 (3)	C14'—H14'	0.9300
C3—H3	0.9300	C15'—H15'	0.9300
C4—C5	1.382 (4)	C16'—H16D	0.9600
C4—C8	1.510 (4)	C16'—H16E	0.9600
C5—C6	1.373 (4)	C16'—H16F	0.9600
C5—H5	0.9300	C17—C18	1.382 (4)
C6—C7	1.377 (4)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.365 (4)
C7—H7	0.9300	C18—H18	0.9300
C8—H8A	0.9600	C19—C20	1.373 (4)
C8—H8B	0.9600	C19—H19	0.9300
C8—H8C	0.9600	C20—C21	1.383 (3)
O3—C9	1.277 (5)	C20—H20	0.9300
O4—C9	1.250 (5)	C21—C22	1.478 (3)
C9—C10	1.508 (5)	C22—C23	1.387 (3)
C10—C11	1.380 (5)	C23—C24	1.379 (4)
C10—C15	1.384 (5)	C23—H23	0.9300
C11—C12	1.395 (6)	C24—C25	1.367 (4)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.377 (7)	C25—C26	1.373 (4)
C12—C16	1.499 (7)	C25—H25	0.9300
C13—C14	1.369 (7)	C26—H26	0.9300
C13—H13	0.9300	O5—H5A	0.8517
C14—C15	1.383 (6)	O5—H5B	0.8515
C14—H14	0.9300	O6—H6A	0.82 (7)
C15—H15	0.9300	O6—H6B	0.82 (7)
O3'—Cu1—O1	86.6 (7)	C10—C15—H15	120.4
O3'—Cu1—N1	170.4 (5)	C12—C16—H16A	109.5
O1—Cu1—N1	94.41 (7)	C12—C16—H16B	109.5
O1—Cu1—O3	91.9 (4)	H16A—C16—H16B	109.5
N1—Cu1—O3	164.9 (3)	C12—C16—H16C	109.5
O3'—Cu1—N2	96.6 (7)	H16A—C16—H16C	109.5
O1—Cu1—N2	168.42 (7)	H16B—C16—H16C	109.5
N1—Cu1—N2	80.58 (7)	C9'—O3'—Cu1	114.1 (12)
O3—Cu1—N2	90.7 (3)	O4'—C9'—O3'	124.5 (10)
O3'—Cu1—O5	98.8 (5)	O4'—C9'—C10'	119.3 (9)
O1—Cu1—O5	93.69 (7)	O3'—C9'—C10'	116.1 (9)
N1—Cu1—O5	90.69 (7)	C11'—C10'—C15'	120.5 (7)
O3—Cu1—O5	102.7 (2)	C11'—C10'—C9'	118.6 (7)
N2—Cu1—O5	96.79 (7)	C15'—C10'—C9'	120.9 (7)
C1—O1—Cu1	123.87 (15)	C10'—C11'—C12'	120.8 (8)
C17—N1—C21	118.7 (2)	C10'—C11'—H11'	119.6
C17—N1—Cu1	126.13 (17)	C12'—C11'—H11'	119.6
C21—N1—Cu1	115.18 (14)	C13'—C12'—C11'	117.7 (8)
C26—N2—C22	119.2 (2)	C13'—C12'—C16'	120.1 (8)
C26—N2—Cu1	125.89 (16)	C11'—C12'—C16'	122.0 (9)
C22—N2—Cu1	114.78 (14)	C14'—C13'—C12'	121.9 (8)
O2—C1—O1	124.6 (2)	C14'—C13'—H13'	119.1
O2—C1—C2	118.7 (2)	C12'—C13'—H13'	119.1
O1—C1—C2	116.66 (19)	C13'—C14'—C15'	120.1 (8)
C7—C2—C3	119.0 (2)	C13'—C14'—H14'	119.9
C7—C2—C1	121.8 (2)	C15'—C14'—H14'	119.9
C3—C2—C1	119.2 (2)	C10'—C15'—C14'	118.9 (8)
C4—C3—C2	121.8 (2)	C10'—C15'—H15'	120.5
C4—C3—H3	119.1	C14'—C15'—H15'	120.5
C2—C3—H3	119.1	C12'—C16'—H16D	109.5
C5—C4—C3	117.6 (2)	C12'—C16'—H16E	109.5
C5—C4—C8	121.9 (3)	H16D—C16'—H16E	109.5
C3—C4—C8	120.4 (3)	C12'—C16'—H16F	109.5
C6—C5—C4	121.5 (3)	H16D—C16'—H16F	109.5
C6—C5—H5	119.3	H16E—C16'—H16F	109.5
C4—C5—H5	119.3	N1—C17—C18	122.6 (3)
C5—C6—C7	120.2 (3)	N1—C17—H17	118.7
C5—C6—H6	119.9	C18—C17—H17	118.7
C7—C6—H6	119.9	C19—C18—C17	118.3 (3)
C6—C7—C2	119.9 (2)	C19—C18—H18	120.9
C6—C7—H7	120.1	C17—C18—H18	120.9
C2—C7—H7	120.1	C18—C19—C20	120.2 (2)
C4—C8—H8A	109.5	C18—C19—H19	119.9
C4—C8—H8B	109.5	C20—C19—H19	119.9
H8A—C8—H8B	109.5	C19—C20—C21	118.7 (2)
C4—C8—H8C	109.5	C19—C20—H20	120.7
H8A—C8—H8C	109.5	C21—C20—H20	120.7
H8B—C8—H8C	109.5	N1—C21—C20	121.6 (2)
C9—O3—Cu1	105.6 (6)	N1—C21—C22	114.54 (18)
O4—C9—O3	122.6 (5)	C20—C21—C22	123.8 (2)
O4—C9—C10	120.4 (5)	N2—C22—C23	121.0 (2)
O3—C9—C10	117.0 (5)	N2—C22—C21	114.65 (18)
C11—C10—C15	119.4 (4)	C23—C22—C21	124.4 (2)
C11—C10—C9	120.1 (4)	C24—C23—C22	119.0 (2)
C15—C10—C9	120.5 (4)	C24—C23—H23	120.5
C10—C11—C12	122.1 (5)	C22—C23—H23	120.5
C10—C11—H11	119.0	C25—C24—C23	119.7 (2)
C12—C11—H11	119.0	C25—C24—H24	120.2
C13—C12—C11	116.9 (5)	C23—C24—H24	120.2
C13—C12—C16	122.1 (5)	C24—C25—C26	118.8 (2)
C11—C12—C16	121.0 (5)	C24—C25—H25	120.6
C14—C13—C12	122.0 (5)	C26—C25—H25	120.6
C14—C13—H13	119.0	N2—C26—C25	122.4 (2)
C12—C13—H13	119.0	N2—C26—H26	118.8
C13—C14—C15	120.5 (5)	C25—C26—H26	118.8
C13—C14—H14	119.8	Cu1—O5—H5A	109.4
C15—C14—H14	119.8	Cu1—O5—H5B	109.3
C14—C15—C10	119.2 (5)	H5A—O5—H5B	104.4
C14—C15—H15	120.4	H6A—O6—H6B	126 (9)
Cu1—O1—C1—O2	−36.8 (3)	O4'—C9'—C10'—C15'	−176.9 (19)
Cu1—O1—C1—C2	143.68 (16)	O3'—C9'—C10'—C15'	−1 (2)
O2—C1—C2—C7	170.4 (2)	C15'—C10'—C11'—C12'	0.4 (13)
O1—C1—C2—C7	−10.0 (3)	C9'—C10'—C11'—C12'	−179.2 (10)
O2—C1—C2—C3	−7.7 (3)	C10'—C11'—C12'—C13'	−1.1 (17)
O1—C1—C2—C3	171.8 (2)	C10'—C11'—C12'—C16'	−177.2 (10)
C7—C2—C3—C4	0.3 (4)	C11'—C12'—C13'—C14'	2.3 (19)
C1—C2—C3—C4	178.4 (2)	C16'—C12'—C13'—C14'	178.5 (11)
C2—C3—C4—C5	0.1 (4)	C12'—C13'—C14'—C15'	−2.7 (17)
C2—C3—C4—C8	−179.4 (3)	C11'—C10'—C15'—C14'	−0.7 (13)
C3—C4—C5—C6	−0.2 (5)	C9'—C10'—C15'—C14'	178.9 (9)
C8—C4—C5—C6	179.3 (3)	C13'—C14'—C15'—C10'	1.9 (14)
C4—C5—C6—C7	0.0 (6)	C21—N1—C17—C18	0.3 (3)
C5—C6—C7—C2	0.4 (5)	Cu1—N1—C17—C18	−178.59 (19)
C3—C2—C7—C6	−0.5 (4)	N1—C17—C18—C19	−0.3 (4)
C1—C2—C7—C6	−178.6 (3)	C17—C18—C19—C20	0.3 (4)
Cu1—O3—C9—O4	−2.8 (14)	C18—C19—C20—C21	−0.3 (4)
Cu1—O3—C9—C10	177.9 (6)	C17—N1—C21—C20	−0.3 (3)
O4—C9—C10—C11	168.3 (9)	Cu1—N1—C21—C20	178.71 (16)
O3—C9—C10—C11	−12.4 (11)	C17—N1—C21—C22	−179.34 (19)
O4—C9—C10—C15	−12.5 (11)	Cu1—N1—C21—C22	−0.3 (2)
O3—C9—C10—C15	166.7 (9)	C19—C20—C21—N1	0.3 (3)
C15—C10—C11—C12	−0.5 (7)	C19—C20—C21—C22	179.3 (2)
C9—C10—C11—C12	178.6 (5)	C26—N2—C22—C23	−1.2 (3)
C10—C11—C12—C13	0.4 (8)	Cu1—N2—C22—C23	174.20 (16)
C10—C11—C12—C16	−178.6 (5)	C26—N2—C22—C21	178.66 (18)
C11—C12—C13—C14	−0.2 (9)	Cu1—N2—C22—C21	−5.9 (2)
C16—C12—C13—C14	178.7 (6)	N1—C21—C22—N2	4.1 (2)
C12—C13—C14—C15	0.2 (10)	C20—C21—C22—N2	−174.88 (19)
C13—C14—C15—C10	−0.2 (8)	N1—C21—C22—C23	−175.98 (19)
C11—C10—C15—C14	0.4 (7)	C20—C21—C22—C23	5.0 (3)
C9—C10—C15—C14	−178.7 (5)	N2—C22—C23—C24	0.6 (3)
O1—Cu1—O3'—C9'	−89.7 (18)	C21—C22—C23—C24	−179.2 (2)
N2—Cu1—O3'—C9'	79.1 (18)	C22—C23—C24—C25	0.7 (4)
O5—Cu1—O3'—C9'	177.1 (17)	C23—C24—C25—C26	−1.4 (4)
Cu1—O3'—C9'—O4'	−3 (3)	C22—N2—C26—C25	0.5 (3)
Cu1—O3'—C9'—C10'	−178.4 (11)	Cu1—N2—C26—C25	−174.38 (19)
O4'—C9'—C10'—C11'	3 (2)	C24—C25—C26—N2	0.8 (4)
O3'—C9'—C10'—C11'	178.4 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2	0.85	1.93	2.643 (3)	140
O5—H5B···O4^a^i	0.85	2.09	2.694 (10)	128
C20—H20···O4^a^ii	0.93	2.40	3.324 (10)	171
C23—H23···O4^a^ii	0.93	2.51	3.405 (7)	163
C18—H18···O2^iii	0.93	2.51	3.371 (4)	154
C24—H24···O6^ii	0.93	2.36	3.200 (5)	151
C26—H26···O3^a	0.93	2.48	2.984 (13)	115
C17—H17···O1	0.93	2.59	3.093 (3)	115
C7—H7···O6	0.93	2.72	3.405 (6)	131

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