Bis­[μ-4-fluoro-6-hydroxymethyl-2-(2,5,8-triaza­oct-1-enyl)phenolato]dicopper(II) bis(perchlorate) methanol solvate

The title dinuclear complex, [Cu₂(C₁₂H₁₇FN₃O₂)₂](ClO₄)₂·CH₄O, was synthesized by condensation between diethyl­ene­triamine and 2-form­yl-4-fluoro-6-hydroxy­methyl­phenol in the presence of copper(II). It contains two similar units, which are linked by Cu—O bonds. The approximate planes of the two units are parallel to each other, and π–π inter­action exists between the two units.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.104
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1C    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4A    ...          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl O4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I)

Crystal data

[Cu2(CH4O)(C12H17FN3O2)2(ClO4)]·ClO4	F(000) = 1776
Mr = 866.59	Dx = 1.655 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5049 reflections
a = 8.5227 (7) Å	θ = 2.5–20.0°
b = 33.412 (3) Å	µ = 1.46 mm^−1
c = 12.2415 (10) Å	T = 292 K
β = 93.702 (2)°	Block, black
V = 3478.7 (5) Å^3	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Smart Apex CCD area-detector diffractometer	6805 independent reflections
Radiation source: sealed tube	5377 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.71, Tmax = 0.75	k = −40→41
28629 measured reflections	l = −15→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 1.55P] where P = (Fo^2 + 2Fc^2)/3
6805 reflections	(Δ/σ)max < 0.001
451 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.31 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
Cu1	0.80917 (5)	0.210947 (11)	0.49374 (3)	0.04211 (12)
Cu2	0.91453 (5)	0.093220 (11)	0.80292 (3)	0.04258 (12)
C1	0.9014 (5)	0.28833 (12)	0.5703 (3)	0.0597 (10)
H1A	0.8689	0.3136	0.6008	0.072*
H1B	1.0080	0.2828	0.5986	0.072*
C2	0.8959 (5)	0.29115 (11)	0.4492 (3)	0.0579 (9)
H2C	0.7946	0.3015	0.4216	0.069*
H2D	0.9769	0.3093	0.4272	0.069*
C3	0.8669 (6)	0.24419 (13)	0.2890 (3)	0.0682 (11)
H3A	0.9357	0.2577	0.2408	0.082*
H3B	0.7612	0.2546	0.2750	0.082*
C4	0.8690 (5)	0.19917 (11)	0.2682 (3)	0.0553 (9)
H4C	0.8124	0.1929	0.1990	0.066*
H4D	0.9762	0.1896	0.2659	0.066*
C5	0.7141 (5)	0.14772 (11)	0.3473 (3)	0.0537 (9)
H5D	0.7097	0.1364	0.2778	0.064*
C6	0.6348 (4)	0.12738 (10)	0.4296 (3)	0.0473 (8)
C7	0.5548 (5)	0.09091 (11)	0.3998 (3)	0.0582 (10)
H7A	0.5539	0.0820	0.3279	0.070*
C8	0.4820 (5)	0.06961 (10)	0.4725 (3)	0.0583 (11)
C9	0.4744 (5)	0.08214 (11)	0.5783 (3)	0.0581 (10)
H9A	0.4193	0.0671	0.6269	0.070*
C10	0.5497 (4)	0.11778 (10)	0.6141 (3)	0.0475 (8)
C11	0.6327 (4)	0.14095 (9)	0.5397 (3)	0.0393 (7)
C12	0.5413 (5)	0.13270 (11)	0.7305 (3)	0.0548 (9)
H12A	0.4811	0.1573	0.7296	0.066*
H12B	0.4862	0.1131	0.7722	0.066*
C13	0.9464 (5)	0.12021 (12)	1.0248 (3)	0.0631 (10)
H13A	0.8525	0.1363	1.0299	0.076*
H13B	1.0199	0.1269	1.0859	0.076*
C14	0.9055 (5)	0.07643 (12)	1.0275 (3)	0.0604 (10)
H14A	1.0008	0.0605	1.0334	0.073*
H14B	0.8456	0.0708	1.0904	0.073*
C15	0.7921 (5)	0.02397 (10)	0.8998 (3)	0.0561 (9)
H15A	0.7159	0.0119	0.9453	0.067*
H15B	0.8912	0.0099	0.9117	0.067*
C16	0.7348 (5)	0.02222 (11)	0.7809 (3)	0.0577 (10)
H16A	0.7420	−0.0050	0.7542	0.069*
H16B	0.6256	0.0305	0.7727	0.069*
C17	0.8525 (4)	0.04230 (11)	0.6184 (3)	0.0513 (9)
H17A	0.8045	0.0198	0.5861	0.062*
C18	0.9448 (4)	0.06652 (10)	0.5507 (3)	0.0477 (8)
C19	0.9587 (5)	0.05413 (13)	0.4426 (3)	0.0594 (10)
H19A	0.9118	0.0303	0.4183	0.071*
C20	1.0398 (5)	0.07646 (11)	0.3730 (3)	0.0548 (10)
C21	1.1129 (5)	0.11183 (12)	0.4047 (3)	0.0580 (10)
H21A	1.1701	0.1263	0.3560	0.070*
C22	1.0991 (4)	0.12497 (11)	0.5085 (3)	0.0544 (9)
C23	1.0150 (4)	0.10318 (10)	0.5844 (3)	0.0448 (8)
C24	1.1736 (4)	0.16441 (11)	0.5467 (3)	0.0515 (9)
H24A	1.2565	0.1590	0.6027	0.062*
H24B	1.2210	0.1770	0.4855	0.062*
C25	1.2424 (5)	0.01228 (11)	0.7853 (3)	0.0547 (10)
H25A	1.1551	0.0001	0.7444	0.082*
H25B	1.2950	−0.0075	0.8314	0.082*
H25C	1.3144	0.0230	0.7357	0.082*
F1	0.4054 (3)	0.03519 (6)	0.44226 (17)	0.0598 (6)
F2	1.0536 (2)	0.06329 (6)	0.26696 (15)	0.0535 (5)
N1	0.7950 (4)	0.25582 (8)	0.6029 (2)	0.0543 (8)
H1C	0.6955	0.2649	0.6028	0.065*
H1D	0.8245	0.2471	0.6707	0.065*
N2	0.9211 (4)	0.25103 (9)	0.4037 (2)	0.0536 (7)
H2	1.0258	0.2456	0.4110	0.064*
N3	0.7903 (4)	0.18005 (10)	0.3615 (2)	0.0513 (7)
N4	1.0190 (4)	0.12825 (9)	0.9188 (2)	0.0525 (7)
H4A	1.1227	0.1230	0.9257	0.063*
H4B	1.0062	0.1542	0.9002	0.063*
N5	0.8120 (4)	0.06628 (8)	0.9259 (2)	0.0481 (7)
H5	0.7146	0.0772	0.9301	0.058*
N6	0.8301 (3)	0.04857 (8)	0.7174 (2)	0.0446 (6)
O1	0.6987 (3)	0.17351 (6)	0.57780 (17)	0.0410 (5)
O2	0.6904 (3)	0.13973 (8)	0.7832 (2)	0.0559 (6)
H2B	0.7263	0.1603	0.7523	0.067*
O3	1.0123 (3)	0.11754 (6)	0.68444 (19)	0.0451 (5)
O4	1.0617 (3)	0.19172 (7)	0.5899 (2)	0.0552 (6)
H4F	1.0378	0.1818	0.6506	0.066*
H5C	1.2677	0.0528	0.8839	0.066*
O5	1.1897 (3)	0.04210 (7)	0.84784 (19)	0.0539 (6)
Cl1	1.43836 (13)	0.08952 (3)	1.06477 (9)	0.0667 (3)
Cl2	0.39645 (13)	0.26120 (3)	0.40364 (9)	0.0629 (3)
O11	1.4230 (4)	0.08409 (10)	0.9646 (3)	0.0794 (9)
O12	1.5670 (4)	0.11307 (9)	1.0899 (2)	0.0802 (9)
O13	1.3097 (4)	0.10163 (10)	1.0986 (3)	0.0751 (8)
O14	1.4644 (4)	0.05616 (10)	1.1136 (3)	0.0821 (9)
O21	0.4881 (4)	0.22944 (9)	0.4095 (2)	0.0671 (8)
O22	0.4397 (4)	0.28804 (9)	0.3241 (3)	0.0788 (9)
O23	0.2593 (4)	0.24580 (10)	0.3639 (3)	0.0803 (9)
O24	0.3829 (4)	0.27778 (9)	0.4954 (3)	0.0772 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0458 (2)	0.0399 (2)	0.0405 (2)	0.00271 (17)	0.00157 (17)	0.00409 (16)
Cu2	0.0506 (3)	0.0357 (2)	0.0406 (2)	−0.00597 (17)	−0.00280 (17)	0.00159 (16)
C1	0.059 (2)	0.055 (2)	0.066 (2)	−0.0276 (18)	0.0151 (19)	−0.0023 (18)
C2	0.048 (2)	0.054 (2)	0.070 (2)	−0.0139 (17)	−0.0034 (18)	0.0071 (18)
C3	0.078 (3)	0.070 (3)	0.059 (2)	0.009 (2)	0.018 (2)	0.018 (2)
C4	0.066 (3)	0.060 (2)	0.0412 (18)	0.0046 (18)	0.0136 (17)	0.0044 (16)
C5	0.052 (2)	0.060 (2)	0.048 (2)	0.0141 (18)	−0.0044 (17)	−0.0092 (17)
C6	0.046 (2)	0.0414 (17)	0.052 (2)	0.0064 (14)	−0.0184 (16)	−0.0032 (14)
C7	0.063 (3)	0.047 (2)	0.061 (2)	0.0086 (18)	−0.0239 (19)	−0.0104 (17)
C8	0.063 (3)	0.0446 (19)	0.062 (2)	−0.0033 (17)	−0.041 (2)	−0.0045 (17)
C9	0.056 (2)	0.051 (2)	0.063 (2)	−0.0149 (17)	−0.0249 (19)	0.0199 (17)
C10	0.0315 (18)	0.0524 (19)	0.057 (2)	0.0047 (14)	−0.0108 (15)	0.0112 (16)
C11	0.0259 (16)	0.0394 (16)	0.0510 (18)	0.0073 (12)	−0.0101 (13)	−0.0003 (13)
C12	0.050 (2)	0.054 (2)	0.060 (2)	−0.0048 (17)	0.0041 (17)	0.0175 (17)
C13	0.074 (3)	0.064 (2)	0.051 (2)	0.013 (2)	0.0041 (19)	−0.0078 (18)
C14	0.073 (3)	0.067 (2)	0.042 (2)	0.009 (2)	0.0047 (18)	0.0102 (17)
C15	0.068 (3)	0.0444 (19)	0.056 (2)	−0.0076 (17)	0.0047 (19)	0.0069 (16)
C16	0.054 (2)	0.046 (2)	0.073 (3)	−0.0082 (16)	0.0025 (19)	0.0038 (17)
C17	0.047 (2)	0.0484 (19)	0.056 (2)	0.0019 (15)	−0.0127 (17)	−0.0113 (16)
C18	0.049 (2)	0.0470 (19)	0.0461 (18)	0.0143 (15)	−0.0022 (15)	−0.0029 (15)
C19	0.052 (2)	0.075 (3)	0.051 (2)	0.0178 (19)	−0.0004 (17)	−0.0030 (19)
C20	0.064 (3)	0.055 (2)	0.0456 (19)	0.0336 (19)	0.0025 (17)	0.0051 (16)
C21	0.059 (3)	0.058 (2)	0.059 (2)	0.0239 (19)	0.0190 (18)	0.0292 (18)
C22	0.041 (2)	0.060 (2)	0.062 (2)	0.0121 (16)	0.0016 (17)	0.0215 (18)
C23	0.043 (2)	0.0457 (18)	0.0445 (18)	0.0171 (15)	−0.0024 (15)	0.0087 (14)
C24	0.043 (2)	0.066 (2)	0.0464 (19)	0.0011 (17)	0.0098 (15)	0.0216 (17)
C25	0.063 (2)	0.052 (2)	0.051 (2)	−0.0306 (18)	0.0140 (18)	−0.0143 (16)
F1	0.0573 (14)	0.0576 (12)	0.0608 (13)	−0.0149 (10)	−0.0244 (10)	−0.0108 (10)
F2	0.0570 (13)	0.0597 (12)	0.0452 (11)	0.0153 (10)	0.0129 (9)	−0.0024 (9)
N1	0.071 (2)	0.0421 (15)	0.0509 (17)	−0.0104 (14)	0.0108 (15)	0.0027 (13)
N2	0.0481 (18)	0.0604 (18)	0.0538 (18)	0.0022 (14)	0.0151 (14)	0.0073 (14)
N3	0.0514 (19)	0.0636 (19)	0.0393 (16)	0.0138 (15)	0.0057 (13)	0.0060 (13)
N4	0.0472 (19)	0.0495 (16)	0.0590 (18)	0.0045 (13)	−0.0116 (14)	−0.0085 (13)
N5	0.0471 (18)	0.0536 (17)	0.0439 (16)	−0.0015 (13)	0.0055 (13)	0.0099 (13)
N6	0.0523 (18)	0.0355 (13)	0.0452 (16)	−0.0019 (12)	−0.0030 (13)	0.0064 (11)
O1	0.0419 (13)	0.0400 (11)	0.0404 (12)	−0.0036 (9)	−0.0027 (10)	−0.0064 (9)
O2	0.0464 (16)	0.0610 (15)	0.0592 (15)	0.0005 (12)	−0.0038 (12)	0.0114 (12)
O3	0.0483 (14)	0.0388 (11)	0.0482 (13)	−0.0077 (10)	0.0035 (10)	0.0006 (10)
O4	0.0387 (14)	0.0623 (15)	0.0640 (16)	0.0040 (12)	−0.0011 (11)	0.0205 (12)
O5	0.0562 (16)	0.0568 (14)	0.0461 (13)	0.0134 (12)	−0.0174 (11)	−0.0113 (11)
Cl1	0.0590 (7)	0.0727 (7)	0.0677 (7)	−0.0121 (5)	−0.0012 (5)	0.0061 (5)
Cl2	0.0643 (7)	0.0608 (6)	0.0634 (6)	0.0007 (5)	0.0016 (5)	0.0105 (5)
O11	0.080 (2)	0.090 (2)	0.068 (2)	−0.0175 (17)	0.0063 (16)	−0.0112 (16)
O12	0.099 (3)	0.0695 (18)	0.0717 (19)	−0.0396 (17)	0.0050 (17)	−0.0233 (15)
O13	0.069 (2)	0.083 (2)	0.0742 (19)	0.0154 (16)	0.0159 (16)	−0.0154 (16)
O14	0.079 (2)	0.082 (2)	0.081 (2)	−0.0234 (17)	−0.0264 (17)	0.0116 (17)
O21	0.0689 (19)	0.0689 (17)	0.0655 (17)	0.0165 (14)	0.0181 (14)	0.0116 (14)
O22	0.074 (2)	0.083 (2)	0.083 (2)	−0.0360 (16)	0.0288 (17)	−0.0019 (16)
O23	0.072 (2)	0.083 (2)	0.084 (2)	−0.0106 (17)	−0.0069 (17)	0.0318 (17)
O24	0.084 (2)	0.0733 (19)	0.077 (2)	−0.0221 (16)	0.0288 (17)	−0.0120 (16)

Geometric parameters (Å, º)

Cu1—O1	1.907 (2)	C14—H14A	0.9700
Cu1—N3	1.918 (3)	C14—H14B	0.9700
Cu1—N2	2.014 (3)	C15—N5	1.457 (4)
Cu1—N1	2.018 (3)	C15—C16	1.507 (5)
Cu2—O3	1.901 (2)	C15—H15A	0.9700
Cu2—N6	1.935 (3)	C15—H15B	0.9700
Cu2—N5	2.003 (3)	C16—N6	1.456 (5)
Cu2—N4	2.003 (3)	C16—H16A	0.9700
Cu1—O4	2.471 (3)	C16—H16B	0.9700
Cu1—O21	2.927 (3)	C17—N6	1.256 (4)
Cu2—O2	2.462 (3)	C17—C18	1.430 (5)
Cu2—O5	2.925 (3)	C17—H17A	0.9300
C1—C2	1.483 (5)	C18—C19	1.399 (5)
C1—N1	1.486 (4)	C18—C23	1.413 (5)
C1—H1A	0.9700	C19—C20	1.356 (6)
C1—H1B	0.9700	C19—H19A	0.9300
C2—N2	1.473 (5)	C20—C21	1.380 (6)
C2—H2C	0.9700	C20—F2	1.383 (4)
C2—H2D	0.9700	C21—C22	1.358 (6)
C3—N2	1.468 (5)	C21—H21A	0.9300
C3—C4	1.526 (6)	C22—C23	1.412 (5)
C3—H3A	0.9700	C22—C24	1.523 (6)
C3—H3B	0.9700	C23—O3	1.316 (4)
C4—N3	1.504 (4)	C24—O4	1.445 (4)
C4—H4C	0.9700	C24—H24A	0.9700
C4—H4D	0.9700	C24—H24B	0.9700
C5—N3	1.267 (5)	C25—O5	1.351 (4)
C5—C6	1.422 (5)	C25—H25A	0.9600
C5—H5D	0.9300	C25—H25B	0.9600
C6—C11	1.423 (5)	C25—H25C	0.9600
C6—C7	1.432 (5)	N1—H1C	0.9000
C7—C8	1.324 (6)	N1—H1D	0.9000
C7—H7A	0.9300	N2—H2	0.9100
C8—F1	1.362 (4)	N4—H4A	0.9000
C8—C9	1.366 (6)	N4—H4B	0.9000
C9—C10	1.409 (5)	N5—H5	0.9100
C9—H9A	0.9300	O2—H2B	0.8500
C10—C11	1.418 (5)	O4—H4F	0.8501
C10—C12	1.516 (5)	O5—H5C	0.8531
C11—O1	1.297 (4)	Cl1—O11	1.239 (3)
C12—O2	1.407 (4)	Cl1—O13	1.263 (3)
C12—H12A	0.9700	Cl1—O14	1.278 (3)
C12—H12B	0.9700	Cl1—O12	1.368 (3)
C13—N4	1.497 (5)	Cl2—O24	1.264 (3)
C13—C14	1.504 (6)	Cl2—O21	1.317 (3)
C13—H13A	0.9700	Cl2—O23	1.340 (3)
C13—H13B	0.9700	Cl2—O22	1.390 (3)
C14—N5	1.472 (5)
O1—Cu1—N3	94.87 (11)	N6—C16—H16B	109.7
O1—Cu1—N2	178.67 (12)	C15—C16—H16B	109.7
N3—Cu1—N2	85.00 (13)	H16A—C16—H16B	108.2
O1—Cu1—N1	94.43 (10)	N6—C17—C18	126.0 (3)
N3—Cu1—N1	162.54 (13)	N6—C17—H17A	117.0
N2—Cu1—N1	85.37 (12)	C18—C17—H17A	117.0
O3—Cu2—N6	94.74 (11)	C19—C18—C23	118.2 (4)
O3—Cu2—N5	178.59 (11)	C19—C18—C17	117.6 (3)
N6—Cu2—N5	84.00 (12)	C23—C18—C17	124.0 (3)
O3—Cu2—N4	95.39 (12)	C20—C19—C18	120.6 (4)
N6—Cu2—N4	165.18 (12)	C20—C19—H19A	119.7
N5—Cu2—N4	85.74 (13)	C18—C19—H19A	119.7
C2—C1—N1	109.6 (3)	C19—C20—C21	122.3 (4)
C2—C1—H1A	109.8	C19—C20—F2	119.5 (4)
N1—C1—H1A	109.8	C21—C20—F2	118.2 (3)
C2—C1—H1B	109.8	C22—C21—C20	118.4 (3)
N1—C1—H1B	109.8	C22—C21—H21A	120.8
H1A—C1—H1B	108.2	C20—C21—H21A	120.8
N2—C2—C1	108.9 (3)	C21—C22—C23	121.9 (4)
N2—C2—H2C	109.9	C21—C22—C24	120.5 (3)
C1—C2—H2C	109.9	C23—C22—C24	117.6 (3)
N2—C2—H2D	109.9	O3—C23—C22	117.6 (3)
C1—C2—H2D	109.9	O3—C23—C18	123.7 (3)
H2C—C2—H2D	108.3	C22—C23—C18	118.6 (3)
N2—C3—C4	107.9 (3)	O4—C24—C22	112.8 (3)
N2—C3—H3A	110.1	O4—C24—H24A	109.0
C4—C3—H3A	110.1	C22—C24—H24A	109.0
N2—C3—H3B	110.1	O4—C24—H24B	109.0
C4—C3—H3B	110.1	C22—C24—H24B	109.0
H3A—C3—H3B	108.4	H24A—C24—H24B	107.8
N3—C4—C3	106.4 (3)	O5—C25—H25A	109.5
N3—C4—H4C	110.5	O5—C25—H25B	109.5
C3—C4—H4C	110.5	H25A—C25—H25B	109.5
N3—C4—H4D	110.5	O5—C25—H25C	109.5
C3—C4—H4D	110.5	H25A—C25—H25C	109.5
H4C—C4—H4D	108.6	H25B—C25—H25C	109.5
N3—C5—C6	125.0 (3)	C1—N1—Cu1	107.5 (2)
N3—C5—H5D	117.5	C1—N1—H1C	110.2
C6—C5—H5D	117.5	Cu1—N1—H1C	110.2
C5—C6—C11	123.7 (3)	C1—N1—H1D	110.2
C5—C6—C7	117.8 (3)	Cu1—N1—H1D	110.2
C11—C6—C7	118.5 (4)	H1C—N1—H1D	108.5
C8—C7—C6	121.5 (4)	C3—N2—C2	117.4 (3)
C8—C7—H7A	119.3	C3—N2—Cu1	106.8 (2)
C6—C7—H7A	119.3	C2—N2—Cu1	108.2 (2)
C7—C8—F1	120.5 (3)	C3—N2—H2	108.0
C7—C8—C9	121.7 (3)	C2—N2—H2	108.0
F1—C8—C9	117.7 (4)	Cu1—N2—H2	108.0
C8—C9—C10	120.3 (4)	C5—N3—C4	120.5 (3)
C8—C9—H9A	119.8	C5—N3—Cu1	126.1 (3)
C10—C9—H9A	119.8	C4—N3—Cu1	113.3 (2)
C9—C10—C11	119.8 (3)	C13—N4—Cu2	108.6 (2)
C9—C10—C12	121.5 (3)	C13—N4—H4A	110.0
C11—C10—C12	118.7 (3)	Cu2—N4—H4A	110.0
O1—C11—C10	116.7 (3)	C13—N4—H4B	110.0
O1—C11—C6	125.1 (3)	Cu2—N4—H4B	110.0
C10—C11—C6	118.1 (3)	H4A—N4—H4B	108.3
O2—C12—C10	113.0 (3)	C15—N5—C14	117.2 (3)
O2—C12—H12A	109.0	C15—N5—Cu2	108.7 (2)
C10—C12—H12A	109.0	C14—N5—Cu2	107.0 (2)
O2—C12—H12B	109.0	C15—N5—H5	107.8
C10—C12—H12B	109.0	C14—N5—H5	107.8
H12A—C12—H12B	107.8	Cu2—N5—H5	107.8
N4—C13—C14	107.6 (3)	C17—N6—C16	122.6 (3)
N4—C13—H13A	110.2	C17—N6—Cu2	125.2 (2)
C14—C13—H13A	110.2	C16—N6—Cu2	112.2 (2)
N4—C13—H13B	110.2	C11—O1—Cu1	125.0 (2)
C14—C13—H13B	110.2	C12—O2—H2B	105.7
H13A—C13—H13B	108.5	C23—O3—Cu2	126.0 (2)
N5—C14—C13	108.6 (3)	C24—O4—H4F	105.9
N5—C14—H14A	110.0	C25—O5—H5C	109.1
C13—C14—H14A	110.0	O11—Cl1—O13	109.4 (2)
N5—C14—H14B	110.0	O11—Cl1—O14	109.8 (2)
C13—C14—H14B	110.0	O13—Cl1—O14	104.7 (2)
H14A—C14—H14B	108.3	O11—Cl1—O12	109.8 (2)
N5—C15—C16	106.0 (3)	O13—Cl1—O12	116.2 (2)
N5—C15—H15A	110.5	O14—Cl1—O12	106.5 (2)
C16—C15—H15A	110.5	O24—Cl2—O21	113.1 (2)
N5—C15—H15B	110.5	O24—Cl2—O23	111.3 (2)
C16—C15—H15B	110.5	O21—Cl2—O23	102.2 (2)
H15A—C15—H15B	108.7	O24—Cl2—O22	112.5 (2)
N6—C16—C15	109.6 (3)	O21—Cl2—O22	112.0 (2)
N6—C16—H16A	109.7	O23—Cl2—O22	104.9 (2)
C15—C16—H16A	109.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O22^i	0.90	2.37	3.251 (5)	165
N1—H1D···O23^i	0.90	2.47	3.228 (4)	142
N4—H4B···O22^i	0.90	2.20	3.086 (4)	167
N2—H2···O23^ii	0.91	2.11	2.959 (5)	156
N5—H5···O11^iii	0.91	2.56	3.430 (5)	161
O4—H4F···O22^i	0.85	2.54	3.185 (4)	133
O2—H2B···O1	0.85	2.18	2.762 (3)	126
O4—H4F···O3	0.85	2.20	2.779 (3)	125
O5—H5C···O11	0.85	1.91	2.756 (4)	171

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