A new copper(II) supra­molecular coordination polymer and a dinuclear compound with multifunctional 2-amino-5-sulfo­benzoic acid and flexible N-donor ligands: synthesis, structure and characterization

Multifunctional 2-amino-5-sulfo­benzoic acid (H₂afsb) can exhibit a variety of roles during the construction of supra­molecular coordination polymers. The pendant carb­oxy­lic acid, sulfonic acid and amino groups could not only play a role in directing bonding but could also have the potential to act as hydrogen-bond donors and acceptors, resulting in extended high-dimensional supra­mole­cular networks. Two new Cu^II coordination compounds, namely catena-poly[[[di­aqua­copper(II)]-μ-1,6-bis­(1H-1,2,4-triazol-1-yl)hexane-κ²N⁴:N^4′] bis­(3-amino-4-carb­oxy­benzene­sulfonate) dihydrate], {[Cu(C₁₀H₁₆N₆)₂(H₂O)₂](C₇H₆NO₅S)₂·2H₂O}_n or {[Cu(bth)₂(H₂O)₂](Hafsb)₂·2H₂O}_n, (1), and bis­(μ-2-amino-5-sul­fon­ato­benzoato-κ²O¹:O^1′)bis­{μ-1,2-bis­[(1H-imidazol-1-yl)meth­yl]benzene-κ²N³:N^3′}bis­[aqua­copper(II)] trihydrate, [Cu₂(C₇H₅NO₅S)₂(C₁₄H₁₄N₄)₂(H₂O)₂]·3H₂O or [Cu₂(afsb)₂(obix)₂(H₂O)₂]·3H₂O, (2), have been obtained through the assembly between H₂afsb and the Cu^II ion in the presence of the flexible N-donor ligands 1,6-bis­(1H-1,2,4-triazol-1-yl)hexane (bth) and 1,2-bis­[(1H-1,2,4-triazol-1-yl)meth­yl]benzene (obix), respectively. Compound (1) consists of a cationic co­or­dination polymeric chain and 3-amino-4-carb­oxy­benzene­sulfonate (Hafsb⁻) anions. Com­pound (2) exhibits an asymmetric dinuclear structure. There are hydrogen-bonded networks within the lattices of (1) and (2). Inter­estingly, both (1) and (2) exhibit reversible dehydration–rehydration behaviour.

Computing details

For both structures, data collection: SMART (Bruker, 2008); cell refinement: SMART (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: Mercury (Macrae et al., 2008).

catena-Poly[[diaquacopper(II)-µ-1,6-bis(1H-1,2,4-triazol-1-yl)hexane-κ²N⁴:N^4'] bis(3-amino-4-carboxybenzenesulfonate) dihydrate] (001)

Crystal data

[Cu(C10H16N6)2(H2O)2](C7H6NO5S)2·2H2O	Dx = 1.427 Mg m^−3
Mr = 1008.55	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pba2	Cell parameters from 9920 reflections
a = 13.7110 (14) Å	θ = 2.6–27.4°
b = 19.1598 (19) Å	µ = 0.63 mm^−1
c = 8.9327 (8) Å	T = 296 K
V = 2346.6 (4) Å^3	Massive, blue
Z = 2	0.3 × 0.25 × 0.2 mm
F(000) = 1054

Data collection

CCD area detector diffractometer	4419 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.026
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2008)	θmax = 27.5°, θmin = 1.1°
Tmin = 0.828, Tmax = 0.882	h = −13→17
20614 measured reflections	k = −24→24
5240 independent reflections	l = −11→11

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.1297P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.30 e Å^−3
5240 reflections	Δρmin = −0.17 e Å^−3
296 parameters	Absolute structure: Flack x determined using 1740 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.003 (6)

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.

Refinement. Refined as a 2-component twin

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

	x	y	z	Uiso*/Ueq
C1	0.1624 (3)	0.90465 (19)	0.8446 (4)	0.0601 (9)
H1	0.129851	0.895428	0.933794	0.072*
C2	0.1950 (2)	0.94757 (17)	0.6347 (4)	0.0505 (7)
H2	0.192804	0.973160	0.546285	0.061*
C3	0.3511 (3)	0.8832 (2)	0.5886 (5)	0.0666 (10)
H3A	0.356550	0.912201	0.499975	0.080*
H3B	0.343067	0.835253	0.556156	0.080*
C4	0.4439 (3)	0.8893 (2)	0.6792 (5)	0.0674 (10)
H4A	0.442899	0.855455	0.760020	0.081*
H4B	0.448043	0.935517	0.722990	0.081*
C5	0.5326 (3)	0.8764 (3)	0.5797 (5)	0.0781 (12)
H5A	0.538042	0.913901	0.507339	0.094*
H5B	0.523451	0.833124	0.524951	0.094*
C6	0.6274 (3)	0.8719 (2)	0.6706 (5)	0.0674 (10)
H6A	0.681578	0.884956	0.606605	0.081*
H6B	0.624328	0.905346	0.751917	0.081*
C7	0.6469 (2)	0.80038 (17)	0.7348 (5)	0.0614 (8)
H7A	0.662471	0.768751	0.653450	0.074*
H7B	0.587773	0.783484	0.782248	0.074*
C8	0.7292 (2)	0.79852 (18)	0.8482 (4)	0.0552 (8)
H8A	0.708689	0.822491	0.938550	0.066*
H8B	0.743115	0.750396	0.874260	0.066*
C9	0.9413 (3)	0.84857 (16)	0.6597 (5)	0.0594 (9)
H9	0.991834	0.842399	0.591617	0.071*
C10	0.8497 (2)	0.89557 (16)	0.8173 (4)	0.0482 (7)
H10	0.820187	0.927118	0.882163	0.058*
C11	0.8215 (2)	0.68972 (15)	0.2055 (4)	0.0468 (7)
C12	0.7237 (2)	0.67469 (14)	0.2423 (4)	0.0503 (7)
C13	0.6631 (2)	0.73038 (18)	0.2821 (4)	0.0579 (9)
H13	0.597941	0.721760	0.304079	0.070*
C14	0.6975 (2)	0.79707 (17)	0.2893 (4)	0.0539 (8)
H14	0.656068	0.833097	0.317896	0.065*
C15	0.7950 (2)	0.81165 (14)	0.2539 (4)	0.0453 (7)
C16	0.8551 (2)	0.75859 (14)	0.2110 (4)	0.0448 (7)
H16	0.919317	0.768350	0.184899	0.054*
C17	0.8904 (3)	0.63429 (18)	0.1629 (5)	0.0608 (9)
Cu1	0.000000	1.000000	0.73657 (8)	0.04232 (14)
N1	0.12802 (15)	0.94891 (11)	0.7404 (3)	0.0455 (5)
N2	0.2454 (2)	0.87580 (18)	0.8094 (4)	0.0687 (9)
N3	0.26582 (19)	0.90431 (14)	0.6733 (3)	0.0522 (7)
N4	0.81759 (18)	0.83127 (13)	0.7908 (3)	0.0482 (6)
N5	0.8757 (2)	0.80055 (14)	0.6880 (4)	0.0635 (8)
N6	0.92825 (15)	0.90826 (11)	0.7395 (3)	0.0462 (5)
N7	0.6852 (2)	0.60838 (14)	0.2410 (5)	0.0675 (8)
H7C	0.625113	0.601875	0.264899	0.081*
H7D	0.721213	0.573465	0.216698	0.081*
O1	0.8713 (2)	0.57288 (13)	0.1721 (5)	0.0995 (12)
O2	0.9758 (2)	0.65620 (14)	0.1184 (4)	0.0811 (9)
H2A	1.010637	0.622503	0.099914	0.122*
O3	0.8047 (3)	0.92748 (15)	0.4013 (3)	0.0897 (10)
O4	0.94143 (19)	0.89604 (12)	0.2459 (7)	0.1211 (17)
O5	0.7917 (3)	0.93515 (14)	0.1366 (3)	0.0781 (8)
O1W	0.000000	1.000000	1.0120 (5)	0.0684 (13)
H1W	−0.023600	0.971200	1.074324	0.103*
O2W	0.000000	1.000000	0.4774 (5)	0.0692 (13)
H2W	−0.026300	0.968500	0.424974	0.104*
O3W	0.0996 (3)	0.55755 (15)	0.0546 (4)	0.0913 (10)
H3WA	0.088797	0.514210	0.049020	0.137*
H3WB	0.158097	0.565110	0.080710	0.137*
S1	0.83731 (6)	0.89868 (4)	0.26184 (11)	0.0558 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.056 (2)	0.060 (2)	0.064 (2)	0.0082 (16)	0.0095 (16)	0.0184 (18)
C2	0.0434 (16)	0.0521 (18)	0.0560 (19)	0.0068 (13)	−0.0012 (14)	0.0096 (15)
C3	0.0509 (19)	0.079 (2)	0.070 (2)	0.0161 (17)	0.0007 (17)	−0.004 (2)
C4	0.0470 (19)	0.089 (3)	0.066 (2)	0.0105 (17)	0.0013 (16)	−0.0049 (19)
C5	0.051 (2)	0.114 (3)	0.069 (3)	0.014 (2)	0.0084 (19)	0.007 (2)
C6	0.0437 (18)	0.081 (2)	0.077 (2)	0.0014 (17)	0.0042 (17)	0.000 (2)
C7	0.0504 (16)	0.0588 (18)	0.075 (2)	−0.0131 (13)	0.0014 (19)	−0.005 (2)
C8	0.0530 (18)	0.0469 (18)	0.066 (2)	−0.0142 (14)	0.0022 (15)	0.0044 (16)
C9	0.0512 (19)	0.0419 (17)	0.085 (2)	0.0019 (14)	0.0109 (16)	−0.0081 (17)
C10	0.0464 (16)	0.0438 (17)	0.0545 (19)	−0.0070 (12)	0.0015 (14)	−0.0059 (14)
C11	0.0517 (16)	0.0384 (14)	0.0502 (18)	−0.0059 (11)	−0.0038 (13)	−0.0002 (13)
C12	0.0558 (16)	0.0437 (14)	0.0513 (17)	−0.0146 (12)	−0.0071 (17)	0.0011 (17)
C13	0.0458 (16)	0.061 (2)	0.067 (2)	−0.0135 (14)	0.0058 (15)	0.0020 (18)
C14	0.0480 (16)	0.0501 (17)	0.064 (2)	−0.0044 (13)	0.0089 (14)	−0.0090 (16)
C15	0.0508 (14)	0.0375 (13)	0.0477 (17)	−0.0085 (11)	0.0015 (14)	−0.0055 (15)
C16	0.0435 (14)	0.0429 (15)	0.0480 (19)	−0.0084 (11)	−0.0015 (13)	−0.0022 (14)
C17	0.060 (2)	0.0460 (18)	0.077 (2)	−0.0038 (15)	−0.0021 (18)	−0.0017 (17)
Cu1	0.0338 (2)	0.0362 (2)	0.0571 (3)	−0.00195 (16)	0.000	0.000
N1	0.0376 (10)	0.0406 (11)	0.0582 (14)	0.0006 (9)	−0.0012 (13)	0.0062 (14)
N2	0.0607 (19)	0.072 (2)	0.073 (2)	0.0187 (15)	0.0065 (16)	0.0218 (17)
N3	0.0412 (14)	0.0548 (16)	0.0605 (16)	0.0092 (11)	0.0004 (12)	0.0039 (13)
N4	0.0460 (13)	0.0379 (12)	0.0605 (16)	−0.0065 (10)	−0.0037 (12)	0.0004 (12)
N5	0.0618 (17)	0.0387 (13)	0.090 (2)	−0.0017 (12)	0.0112 (15)	−0.0098 (14)
N6	0.0402 (11)	0.0411 (12)	0.0573 (14)	−0.0026 (9)	−0.0015 (13)	−0.0017 (13)
N7	0.0647 (17)	0.0470 (14)	0.091 (2)	−0.0210 (11)	0.002 (2)	−0.001 (2)
O1	0.088 (2)	0.0361 (13)	0.174 (4)	−0.0072 (12)	0.026 (2)	−0.0093 (17)
O2	0.0645 (16)	0.0448 (14)	0.134 (3)	0.0034 (11)	0.0197 (17)	0.0005 (16)
O3	0.146 (3)	0.0552 (16)	0.0676 (17)	−0.0180 (17)	0.0059 (18)	−0.0221 (14)
O4	0.0528 (14)	0.0509 (14)	0.260 (5)	−0.0154 (11)	0.014 (3)	−0.013 (3)
O5	0.114 (2)	0.0502 (15)	0.0701 (17)	−0.0101 (14)	0.0084 (16)	0.0074 (14)
O1W	0.075 (3)	0.076 (3)	0.054 (2)	−0.0265 (18)	0.000	0.000
O2W	0.065 (3)	0.090 (4)	0.053 (2)	−0.0332 (19)	0.000	0.000
O3W	0.091 (2)	0.0529 (15)	0.130 (3)	0.0140 (14)	0.021 (2)	0.0144 (18)
S1	0.0580 (4)	0.0375 (4)	0.0720 (6)	−0.0098 (3)	0.0069 (4)	−0.0083 (4)

Geometric parameters (Å, º)

C1—N2	1.303 (5)	C11—C17	1.471 (5)
C1—N1	1.344 (4)	C12—N7	1.376 (4)
C1—H1	0.9300	C12—C13	1.398 (5)
C2—N1	1.318 (4)	C13—C14	1.364 (5)
C2—N3	1.322 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.402 (4)
C3—N3	1.450 (5)	C14—H14	0.9300
C3—C4	1.512 (5)	C15—C16	1.363 (4)
C3—H3A	0.9700	C15—S1	1.767 (3)
C3—H3B	0.9700	C16—H16	0.9300
C4—C5	1.527 (6)	C17—O1	1.208 (4)
C4—H4A	0.9700	C17—O2	1.307 (5)
C4—H4B	0.9700	Cu1—N1	2.010 (2)
C5—C6	1.535 (6)	Cu1—N1^i	2.010 (2)
C5—H5A	0.9700	Cu1—N6^ii	2.015 (2)
C5—H5B	0.9700	Cu1—N6^iii	2.015 (2)
C6—C7	1.509 (6)	Cu1—O2W	2.315 (4)
C6—H6A	0.9700	Cu1—O1W	2.461 (4)
C6—H6B	0.9700	N2—N3	1.362 (4)
C7—C8	1.517 (5)	N4—N5	1.351 (4)
C7—H7A	0.9700	N7—H7C	0.8603
C7—H7B	0.9700	N7—H7D	0.8591
C8—N4	1.458 (4)	O2—H2A	0.8197
C8—H8A	0.9700	O3—S1	1.434 (3)
C8—H8B	0.9700	O4—S1	1.436 (3)
C9—N5	1.311 (4)	O5—S1	1.460 (3)
C9—N6	1.359 (4)	O1W—H1W	0.8479
C9—H9	0.9300	O1W—H1W^i	0.8479
C10—N6	1.305 (4)	O2W—H2W	0.8446
C10—N4	1.329 (4)	O2W—H2W^i	0.8446
C10—H10	0.9300	O3W—H3WA	0.8450
C11—C16	1.398 (4)	O3W—H3WB	0.8478
C11—C12	1.411 (4)
N2—C1—N1	114.0 (3)	C13—C14—H14	119.8
N2—C1—H1	123.0	C15—C14—H14	119.8
N1—C1—H1	123.0	C16—C15—C14	119.4 (3)
N1—C2—N3	109.7 (3)	C16—C15—S1	121.1 (2)
N1—C2—H2	125.2	C14—C15—S1	119.5 (2)
N3—C2—H2	125.2	C15—C16—C11	121.0 (3)
N3—C3—C4	112.2 (3)	C15—C16—H16	119.5
N3—C3—H3A	109.2	C11—C16—H16	119.5
C4—C3—H3A	109.2	O1—C17—O2	121.9 (3)
N3—C3—H3B	109.2	O1—C17—C11	123.1 (3)
C4—C3—H3B	109.2	O2—C17—C11	115.0 (3)
H3A—C3—H3B	107.9	N1—Cu1—N1^i	178.03 (18)
C3—C4—C5	110.2 (4)	N1—Cu1—N6^ii	89.90 (9)
C3—C4—H4A	109.6	N1^i—Cu1—N6^ii	90.08 (9)
C5—C4—H4A	109.6	N1—Cu1—N6^iii	90.08 (9)
C3—C4—H4B	109.6	N1^i—Cu1—N6^iii	89.90 (9)
C5—C4—H4B	109.6	N6^ii—Cu1—N6^iii	178.52 (18)
H4A—C4—H4B	108.1	N1—Cu1—O2W	90.98 (9)
C4—C5—C6	112.1 (4)	N1^i—Cu1—O2W	90.98 (9)
C4—C5—H5A	109.2	N6^ii—Cu1—O2W	90.74 (9)
C6—C5—H5A	109.2	N6^iii—Cu1—O2W	90.74 (9)
C4—C5—H5B	109.2	N1—Cu1—O1W	89.02 (9)
C6—C5—H5B	109.2	N1^i—Cu1—O1W	89.02 (9)
H5A—C5—H5B	107.9	N6^ii—Cu1—O1W	89.26 (9)
C7—C6—C5	113.7 (4)	N6^iii—Cu1—O1W	89.26 (9)
C7—C6—H6A	108.8	O2W—Cu1—O1W	180.0
C5—C6—H6A	108.8	C2—N1—C1	103.9 (3)
C7—C6—H6B	108.8	C2—N1—Cu1	127.3 (2)
C5—C6—H6B	108.8	C1—N1—Cu1	128.7 (2)
H6A—C6—H6B	107.7	C1—N2—N3	103.0 (3)
C6—C7—C8	114.0 (3)	C2—N3—N2	109.5 (3)
C6—C7—H7A	108.8	C2—N3—C3	129.1 (3)
C8—C7—H7A	108.8	N2—N3—C3	121.3 (3)
C6—C7—H7B	108.8	C10—N4—N5	109.2 (3)
C8—C7—H7B	108.8	C10—N4—C8	127.7 (3)
H7A—C7—H7B	107.6	N5—N4—C8	122.8 (2)
N4—C8—C7	111.9 (3)	C9—N5—N4	103.3 (3)
N4—C8—H8A	109.2	C10—N6—C9	103.3 (2)
C7—C8—H8A	109.2	C10—N6—Cu1^iv	124.9 (2)
N4—C8—H8B	109.2	C9—N6—Cu1^iv	131.5 (2)
C7—C8—H8B	109.2	C12—N7—H7C	119.9
H8A—C8—H8B	107.9	C12—N7—H7D	120.1
N5—C9—N6	113.6 (3)	H7C—N7—H7D	120.0
N5—C9—H9	123.2	C17—O2—H2A	109.3
N6—C9—H9	123.2	Cu1—O1W—H1W	131.0
N6—C10—N4	110.6 (3)	Cu1—O1W—H1W^i	131.024 (4)
N6—C10—H10	124.7	H1W—O1W—H1W^i	98.0
N4—C10—H10	124.7	Cu1—O2W—H2W	123.7
C16—C11—C12	119.8 (3)	Cu1—O2W—H2W^i	123.655 (3)
C16—C11—C17	118.6 (3)	H2W—O2W—H2W^i	112.7
C12—C11—C17	121.5 (3)	H3WA—O3W—H3WB	110.5
N7—C12—C13	118.7 (3)	O3—S1—O4	114.2 (3)
N7—C12—C11	123.4 (3)	O3—S1—O5	110.4 (2)
C13—C12—C11	117.9 (3)	O4—S1—O5	111.5 (3)
C14—C13—C12	121.5 (3)	O3—S1—C15	107.19 (18)
C14—C13—H13	119.3	O4—S1—C15	106.80 (14)
C12—C13—H13	119.3	O5—S1—C15	106.30 (16)
C13—C14—C15	120.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N2^v	0.97	2.49	3.365 (5)	151
N7—H7C···O4^vi	0.86	2.52	3.344 (4)	160
O3W—H3WB···O5^vi	0.85	1.90	2.737 (5)	170
O3W—H3WA···O1^vii	0.84	2.07	2.740 (4)	136
O2—H2A···O3W^iv	0.82	1.79	2.603 (4)	172
O2W—H2W···O4^iii	0.84	2.16	2.981 (6)	163
O2W—H2W···O3^iii	0.84	2.46	3.092 (4)	133
O1W—H1W···O4^viii	0.85	2.16	2.996 (6)	170

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

Bis(µ-2-amino-5-sulfonatobenzoato-κ²O¹:O^1')bis{µ-1,2-bis[(1H-imidazol-1-yl)methyl]benzene-κ²N³:N^3'}bis[aquacopper(II)] trihydrate (002)

Crystal data

[Cu2(C7H5NO5S)2(C14H14N4)2(H2O)2]·3H2O	F(000) = 2320
Mr = 1124.10	Dx = 1.619 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.787 (2) Å	Cell parameters from 9870 reflections
b = 12.0409 (12) Å	θ = 2.2–27.4°
c = 20.699 (2) Å	µ = 1.09 mm^−1
β = 99.905 (4)°	T = 293 K
V = 4612.6 (8) Å^3	Massive, green
Z = 4	0.26 × 0.25 × 0.22 mm

Data collection

CCD area detector diffractometer	7450 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.040
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2008)	θmax = 27.5°, θmin = 2.0°
Tmin = 0.760, Tmax = 0.786	h = −24→22
47208 measured reflections	k = −15→15
10554 independent reflections	l = −22→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 3.4892P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
10554 reflections	Δρmax = 0.74 e Å^−3
640 parameters	Δρmin = −0.78 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
C1	0.86921 (13)	1.1781 (2)	1.12680 (13)	0.0255 (6)
C2	0.89216 (15)	1.1639 (2)	1.19508 (14)	0.0310 (6)
C3	0.91954 (17)	1.2574 (2)	1.23217 (14)	0.0370 (7)
H3	0.935213	1.249487	1.277055	0.044*
C4	0.92371 (16)	1.3593 (2)	1.20401 (14)	0.0352 (7)
H4	0.941930	1.419394	1.229870	0.042*
C5	0.90099 (14)	1.3737 (2)	1.13720 (14)	0.0289 (6)
C6	0.87424 (14)	1.2832 (2)	1.09968 (13)	0.0268 (6)
H6	0.859071	1.292770	1.054837	0.032*
C7	0.83654 (14)	1.0871 (2)	1.08145 (14)	0.0276 (6)
C8	0.67367 (15)	1.2209 (2)	1.00930 (14)	0.0304 (6)
H8	0.713774	1.232767	1.041736	0.037*
C9	0.56369 (16)	1.2236 (3)	0.95644 (16)	0.0411 (8)
H9	0.514309	1.236385	0.944954	0.049*
C10	0.60638 (16)	1.1720 (3)	0.91948 (16)	0.0409 (8)
H10	0.591092	1.142680	0.877843	0.049*
C11	0.58234 (17)	1.3181 (3)	1.06622 (15)	0.0404 (7)
H11A	0.537096	1.287362	1.074633	0.049*
H11B	0.573178	1.393930	1.051223	0.049*
C12	0.63549 (15)	1.3194 (2)	1.12894 (14)	0.0311 (6)
C13	0.63425 (15)	1.2414 (2)	1.17913 (14)	0.0299 (6)
C14	0.68443 (17)	1.2496 (3)	1.23635 (15)	0.0399 (7)
H14	0.683355	1.198565	1.269894	0.048*
C15	0.73598 (18)	1.3323 (3)	1.24437 (17)	0.0478 (9)
H15	0.769723	1.336213	1.282854	0.057*
C16	0.73737 (18)	1.4086 (3)	1.19554 (18)	0.0478 (9)
H16	0.772209	1.464242	1.200826	0.057*
C17	0.68722 (17)	1.4030 (2)	1.13858 (17)	0.0410 (8)
H17	0.688020	1.456112	1.106068	0.049*
C18	0.58280 (17)	1.1449 (2)	1.17130 (16)	0.0374 (7)
H18A	0.580889	1.112848	1.213962	0.045*
H18B	0.534708	1.170705	1.152758	0.045*
C19	0.67366 (15)	1.0339 (2)	1.12209 (14)	0.0305 (6)
H19	0.714405	1.067703	1.145944	0.037*
C20	0.60505 (18)	0.9284 (3)	1.05549 (19)	0.0530 (9)
H20	0.589058	0.874851	1.023952	0.064*
C21	0.56216 (18)	0.9921 (3)	1.0862 (2)	0.0534 (10)
H21	0.511952	0.990316	1.079787	0.064*
C22	0.62813 (13)	0.8210 (2)	0.85464 (12)	0.0226 (5)
C23	0.59604 (13)	0.8469 (2)	0.78963 (13)	0.0251 (6)
C24	0.55254 (15)	0.7649 (2)	0.75305 (14)	0.0306 (6)
H24	0.529988	0.781028	0.710493	0.037*
C25	0.54288 (15)	0.6625 (2)	0.77875 (14)	0.0311 (6)
H25	0.514751	0.609797	0.753280	0.037*
C26	0.57492 (14)	0.6365 (2)	0.84301 (13)	0.0238 (6)
C27	0.61649 (13)	0.7152 (2)	0.87949 (12)	0.0240 (6)
H27	0.637769	0.698064	0.922273	0.029*
C28	0.67575 (13)	0.8989 (2)	0.89909 (13)	0.0254 (6)
C29	0.83651 (16)	0.9462 (2)	0.85162 (14)	0.0338 (7)
H29	0.794516	0.904689	0.840112	0.041*
C30	0.94817 (17)	1.0011 (3)	0.85936 (17)	0.0450 (8)
H30	0.996583	1.005622	0.855163	0.054*
C31	0.91083 (17)	1.0739 (3)	0.89097 (16)	0.0424 (8)
H31	0.929891	1.137976	0.912397	0.051*
C32	0.91608 (19)	0.8209 (3)	0.79701 (17)	0.0466 (8)
H32A	0.960500	0.786786	0.818919	0.056*
H32B	0.923278	0.844160	0.753724	0.056*
C33	0.85592 (17)	0.7372 (2)	0.79038 (15)	0.0367 (7)
C34	0.85259 (18)	0.6550 (2)	0.83744 (15)	0.0387 (7)
C35	0.7930 (2)	0.5842 (3)	0.8290 (2)	0.0570 (11)
H35	0.790228	0.528318	0.859442	0.068*
C36	0.7379 (2)	0.5962 (3)	0.7756 (2)	0.0629 (12)
H36	0.697933	0.549467	0.770907	0.075*
C37	0.7423 (2)	0.6761 (4)	0.7303 (2)	0.0623 (11)
H37	0.705318	0.683986	0.694401	0.075*
C38	0.8008 (2)	0.7447 (3)	0.73715 (16)	0.0512 (9)
H38	0.803566	0.798028	0.705169	0.061*
C39	0.9083 (2)	0.6439 (3)	0.89827 (17)	0.0543 (10)
H39A	0.905487	0.570026	0.916394	0.065*
H39B	0.956022	0.652921	0.887137	0.065*
C40	0.83550 (17)	0.7487 (3)	0.96783 (15)	0.0388 (7)
H40	0.792528	0.711141	0.953130	0.047*
C41	0.91219 (18)	0.8623 (4)	1.01778 (19)	0.0591 (10)
H41	0.933123	0.919071	1.045063	0.071*
C42	0.94700 (18)	0.7993 (4)	0.97891 (18)	0.0591 (11)
H42	0.995299	0.804840	0.974474	0.071*
Cu1	0.75935 (2)	1.10477 (3)	0.92216 (2)	0.02946 (10)
Cu2	0.76041 (2)	0.89423 (3)	1.04557 (2)	0.03086 (10)
N1	0.67600 (12)	1.16985 (19)	0.95330 (11)	0.0303 (5)
N2	0.60666 (12)	1.25333 (18)	1.01373 (11)	0.0280 (5)
N3	0.60573 (12)	1.05910 (19)	1.12809 (12)	0.0308 (5)
N4	0.67560 (12)	0.95488 (19)	1.07792 (12)	0.0315 (5)
N5	0.89258 (17)	1.0633 (2)	1.22539 (13)	0.0556 (8)
H5A	0.909419	1.057533	1.266594	0.083*
H5B	0.876020	1.005605	1.203290	0.083*
N6	0.84047 (12)	1.03843 (19)	0.88643 (11)	0.0300 (5)
N7	0.89982 (13)	0.91953 (19)	0.83485 (12)	0.0331 (5)
N8	0.89774 (14)	0.7268 (2)	0.94779 (12)	0.0394 (6)
N9	0.84222 (13)	0.8300 (2)	1.01092 (12)	0.0352 (6)
N10	0.60322 (15)	0.9475 (2)	0.76169 (13)	0.0438 (7)
H10A	0.628242	0.998879	0.783815	0.066*
H10B	0.582729	0.959763	0.721891	0.066*
O1	0.82157 (12)	1.10717 (17)	1.02207 (10)	0.0412 (5)
O2	0.82486 (10)	0.99374 (16)	1.10700 (10)	0.0338 (5)
O3	0.95690 (18)	1.5696 (2)	1.14177 (14)	0.0776 (9)
O4	0.92283 (17)	1.4881 (2)	1.03698 (13)	0.0711 (8)
O5	0.83108 (16)	1.5489 (2)	1.0933 (2)	0.1032 (13)
O6	0.69428 (10)	0.98941 (15)	0.87518 (10)	0.0325 (5)
O7	0.69515 (11)	0.86864 (17)	0.95701 (10)	0.0389 (5)
O8	0.60268 (11)	0.50267 (16)	0.94180 (10)	0.0367 (5)
O9	0.59960 (13)	0.42735 (17)	0.83275 (11)	0.0458 (6)
O10	0.48886 (10)	0.48052 (17)	0.86896 (10)	0.0365 (5)
O1W	0.79382 (11)	1.26356 (16)	0.90347 (11)	0.0423 (5)
H1WA	0.835856	1.281786	0.896402	0.064*
H1WB	0.774556	1.323006	0.914712	0.064*
O2W	0.73288 (11)	0.72419 (17)	1.07575 (11)	0.0450 (6)
H2WA	0.765890	0.676170	1.078457	0.067*
H2WB	0.691840	0.694270	1.073588	0.067*
O3W	0.59312 (11)	0.86211 (18)	0.54928 (11)	0.0443 (5)
H3WA	0.593378	0.896440	0.513372	0.067*
H3WB	0.567508	0.900150	0.571012	0.067*
O4W	0.92969 (14)	0.3521 (2)	0.92691 (17)	0.0766 (9)
H4WA	0.936966	0.396368	0.958965	0.115*
H4WB	0.957416	0.361618	0.899315	0.115*
O5W	0.75022 (13)	0.4449 (2)	0.96529 (13)	0.0649 (7)
H5WA	0.778876	0.480819	0.993893	0.097*
H5WB	0.707926	0.471069	0.964603	0.097*
S1	0.90347 (4)	1.50651 (6)	1.10037 (4)	0.03859 (19)
S2	0.56619 (4)	0.50074 (5)	0.87364 (3)	0.02652 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0207 (13)	0.0282 (14)	0.0275 (14)	0.0004 (11)	0.0042 (11)	−0.0021 (11)
C2	0.0343 (16)	0.0310 (16)	0.0282 (15)	−0.0025 (12)	0.0068 (12)	0.0004 (12)
C3	0.0491 (19)	0.0368 (17)	0.0242 (15)	−0.0037 (14)	0.0035 (13)	−0.0055 (13)
C4	0.0416 (17)	0.0296 (16)	0.0338 (17)	−0.0037 (13)	0.0047 (13)	−0.0089 (13)
C5	0.0262 (14)	0.0240 (14)	0.0371 (17)	−0.0007 (11)	0.0075 (12)	0.0004 (12)
C6	0.0243 (14)	0.0297 (15)	0.0266 (14)	0.0015 (11)	0.0046 (11)	0.0016 (11)
C7	0.0188 (13)	0.0286 (15)	0.0350 (17)	0.0017 (11)	0.0031 (11)	−0.0074 (12)
C8	0.0265 (15)	0.0319 (15)	0.0321 (16)	0.0009 (12)	0.0027 (12)	−0.0023 (12)
C9	0.0269 (16)	0.0422 (18)	0.052 (2)	0.0030 (13)	0.0003 (14)	−0.0053 (15)
C10	0.0340 (17)	0.0453 (19)	0.0402 (18)	0.0025 (14)	−0.0026 (14)	−0.0114 (15)
C11	0.0394 (17)	0.0425 (18)	0.0419 (18)	0.0144 (14)	0.0140 (14)	0.0018 (14)
C12	0.0342 (16)	0.0291 (15)	0.0328 (16)	0.0074 (12)	0.0135 (12)	−0.0026 (12)
C13	0.0329 (15)	0.0263 (15)	0.0340 (16)	0.0031 (11)	0.0152 (13)	−0.0044 (12)
C14	0.050 (2)	0.0414 (18)	0.0297 (16)	0.0048 (15)	0.0106 (14)	−0.0007 (14)
C15	0.0432 (19)	0.060 (2)	0.0393 (19)	0.0004 (17)	0.0044 (15)	−0.0160 (17)
C16	0.0411 (19)	0.045 (2)	0.062 (2)	−0.0107 (15)	0.0208 (17)	−0.0182 (17)
C17	0.0487 (19)	0.0283 (16)	0.052 (2)	0.0007 (14)	0.0245 (16)	0.0007 (14)
C18	0.0410 (18)	0.0338 (16)	0.0423 (18)	0.0005 (13)	0.0206 (14)	−0.0040 (13)
C19	0.0302 (15)	0.0300 (15)	0.0312 (16)	−0.0015 (12)	0.0050 (12)	−0.0031 (12)
C20	0.0376 (19)	0.050 (2)	0.071 (3)	−0.0089 (16)	0.0070 (17)	−0.0299 (19)
C21	0.0290 (17)	0.048 (2)	0.082 (3)	−0.0086 (15)	0.0076 (17)	−0.0230 (19)
C22	0.0221 (13)	0.0220 (13)	0.0234 (14)	−0.0007 (10)	0.0031 (10)	−0.0033 (10)
C23	0.0226 (13)	0.0261 (14)	0.0264 (14)	−0.0018 (11)	0.0037 (11)	−0.0004 (11)
C24	0.0351 (16)	0.0315 (15)	0.0229 (14)	−0.0023 (12)	−0.0013 (12)	−0.0002 (12)
C25	0.0326 (15)	0.0287 (15)	0.0302 (16)	−0.0066 (12)	0.0005 (12)	−0.0066 (12)
C26	0.0265 (14)	0.0206 (13)	0.0244 (14)	−0.0024 (10)	0.0052 (11)	−0.0008 (10)
C27	0.0251 (13)	0.0259 (14)	0.0199 (13)	−0.0005 (11)	0.0007 (10)	−0.0021 (11)
C28	0.0199 (13)	0.0248 (14)	0.0315 (16)	−0.0002 (11)	0.0044 (11)	−0.0086 (12)
C29	0.0327 (16)	0.0329 (16)	0.0358 (17)	−0.0027 (13)	0.0055 (13)	−0.0047 (13)
C30	0.0334 (17)	0.048 (2)	0.053 (2)	−0.0028 (15)	0.0077 (15)	−0.0066 (16)
C31	0.0348 (17)	0.0418 (18)	0.048 (2)	−0.0013 (14)	0.0002 (14)	−0.0127 (15)
C32	0.055 (2)	0.0400 (19)	0.051 (2)	0.0001 (15)	0.0270 (17)	−0.0104 (15)
C33	0.0500 (19)	0.0273 (15)	0.0353 (17)	0.0052 (13)	0.0147 (14)	−0.0090 (13)
C34	0.055 (2)	0.0279 (16)	0.0376 (18)	0.0099 (14)	0.0193 (15)	−0.0053 (13)
C35	0.086 (3)	0.0355 (19)	0.062 (3)	−0.0043 (18)	0.047 (2)	−0.0078 (17)
C36	0.059 (2)	0.063 (3)	0.073 (3)	−0.019 (2)	0.028 (2)	−0.037 (2)
C37	0.063 (3)	0.069 (3)	0.052 (2)	0.000 (2)	0.0006 (19)	−0.024 (2)
C38	0.075 (3)	0.045 (2)	0.0327 (18)	0.0037 (18)	0.0080 (17)	−0.0064 (15)
C39	0.070 (2)	0.052 (2)	0.043 (2)	0.0326 (19)	0.0159 (18)	0.0020 (17)
C40	0.0409 (18)	0.0384 (18)	0.0379 (18)	0.0023 (14)	0.0089 (14)	−0.0045 (14)
C41	0.0330 (19)	0.079 (3)	0.062 (2)	0.0029 (18)	−0.0015 (17)	−0.026 (2)
C42	0.0308 (18)	0.086 (3)	0.060 (2)	0.0115 (18)	0.0043 (16)	−0.016 (2)
Cu1	0.02727 (19)	0.02813 (19)	0.0329 (2)	−0.00299 (14)	0.00486 (14)	−0.00800 (14)
Cu2	0.02895 (19)	0.0310 (2)	0.0318 (2)	−0.00243 (14)	0.00273 (14)	−0.01002 (15)
N1	0.0291 (12)	0.0287 (13)	0.0334 (13)	−0.0015 (10)	0.0062 (10)	−0.0058 (10)
N2	0.0286 (12)	0.0249 (12)	0.0312 (13)	0.0032 (9)	0.0071 (10)	0.0021 (10)
N3	0.0304 (13)	0.0256 (12)	0.0384 (14)	−0.0046 (10)	0.0114 (11)	−0.0028 (10)
N4	0.0315 (13)	0.0263 (12)	0.0362 (14)	−0.0008 (10)	0.0045 (10)	−0.0040 (10)
N5	0.093 (2)	0.0365 (16)	0.0312 (15)	−0.0182 (15)	−0.0053 (15)	0.0069 (13)
N6	0.0313 (13)	0.0273 (12)	0.0310 (13)	−0.0003 (10)	0.0037 (10)	−0.0045 (10)
N7	0.0339 (13)	0.0293 (13)	0.0376 (14)	0.0000 (10)	0.0106 (11)	−0.0040 (11)
N8	0.0411 (15)	0.0438 (15)	0.0343 (14)	0.0155 (12)	0.0089 (12)	0.0016 (12)
N9	0.0331 (14)	0.0389 (14)	0.0334 (14)	0.0021 (11)	0.0048 (11)	−0.0055 (11)
N10	0.0593 (18)	0.0314 (14)	0.0350 (15)	−0.0130 (12)	−0.0081 (12)	0.0091 (12)
O1	0.0485 (13)	0.0407 (12)	0.0288 (12)	0.0030 (10)	−0.0085 (10)	−0.0052 (9)
O2	0.0360 (11)	0.0279 (11)	0.0365 (11)	−0.0091 (8)	0.0037 (9)	−0.0071 (9)
O3	0.115 (2)	0.0479 (16)	0.0631 (18)	−0.0438 (16)	−0.0038 (16)	0.0023 (14)
O4	0.119 (2)	0.0461 (15)	0.0514 (16)	−0.0130 (15)	0.0235 (16)	0.0113 (12)
O5	0.0651 (19)	0.0551 (18)	0.203 (4)	0.0305 (15)	0.063 (2)	0.062 (2)
O6	0.0333 (11)	0.0239 (10)	0.0396 (12)	−0.0084 (8)	0.0043 (9)	−0.0069 (8)
O7	0.0428 (12)	0.0390 (12)	0.0293 (12)	−0.0060 (9)	−0.0099 (9)	−0.0067 (9)
O8	0.0459 (12)	0.0323 (11)	0.0292 (11)	−0.0011 (9)	−0.0010 (9)	0.0036 (9)
O9	0.0651 (15)	0.0294 (11)	0.0496 (14)	0.0044 (10)	0.0285 (12)	−0.0065 (10)
O10	0.0345 (11)	0.0374 (12)	0.0381 (12)	−0.0108 (9)	0.0075 (9)	0.0014 (9)
O1W	0.0405 (12)	0.0263 (11)	0.0638 (15)	−0.0040 (9)	0.0191 (11)	0.0002 (10)
O2W	0.0388 (12)	0.0294 (11)	0.0664 (16)	0.0031 (9)	0.0083 (11)	0.0099 (11)
O3W	0.0471 (13)	0.0387 (12)	0.0506 (14)	0.0072 (10)	0.0179 (11)	0.0019 (10)
O4W	0.0516 (16)	0.0498 (16)	0.129 (3)	−0.0148 (13)	0.0174 (16)	−0.0197 (17)
O5W	0.0490 (15)	0.0685 (18)	0.0744 (18)	0.0122 (13)	0.0023 (13)	−0.0154 (15)
S1	0.0394 (4)	0.0249 (4)	0.0533 (5)	−0.0010 (3)	0.0132 (4)	0.0048 (3)
S2	0.0332 (4)	0.0214 (3)	0.0258 (3)	−0.0034 (3)	0.0073 (3)	−0.0025 (3)

Geometric parameters (Å, º)

C1—C6	1.394 (4)	C29—N7	1.334 (4)
C1—C2	1.415 (4)	C29—H29	0.9300
C1—C7	1.504 (4)	C30—C31	1.359 (4)
C2—N5	1.364 (4)	C30—N7	1.375 (4)
C2—C3	1.409 (4)	C30—H30	0.9300
C3—C4	1.366 (4)	C31—N6	1.377 (4)
C3—H3	0.9300	C31—H31	0.9300
C4—C5	1.386 (4)	C32—N7	1.483 (4)
C4—H4	0.9300	C32—C33	1.503 (4)
C5—C6	1.381 (4)	C32—H32A	0.9700
C5—S1	1.776 (3)	C32—H32B	0.9700
C6—H6	0.9300	C33—C38	1.379 (5)
C7—O1	1.237 (3)	C33—C34	1.397 (4)
C7—O2	1.277 (3)	C34—C35	1.394 (5)
C8—N1	1.319 (4)	C34—C39	1.498 (5)
C8—N2	1.336 (3)	C35—C36	1.385 (6)
C8—H8	0.9300	C35—H35	0.9300
C9—C10	1.351 (4)	C36—C37	1.357 (6)
C9—N2	1.363 (4)	C36—H36	0.9300
C9—H9	0.9300	C37—C38	1.363 (5)
C10—N1	1.373 (4)	C37—H37	0.9300
C10—H10	0.9300	C38—H38	0.9300
C11—N2	1.473 (4)	C39—N8	1.468 (4)
C11—C12	1.496 (4)	C39—H39A	0.9700
C11—H11A	0.9700	C39—H39B	0.9700
C11—H11B	0.9700	C40—N9	1.316 (4)
C12—C17	1.390 (4)	C40—N8	1.333 (4)
C12—C13	1.404 (4)	C40—H40	0.9300
C13—C14	1.385 (4)	C41—C42	1.353 (5)
C13—C18	1.502 (4)	C41—N9	1.355 (4)
C14—C15	1.379 (5)	C41—H41	0.9300
C14—H14	0.9300	C42—N8	1.352 (5)
C15—C16	1.369 (5)	C42—H42	0.9300
C15—H15	0.9300	Cu1—N1	1.957 (2)
C16—C17	1.379 (5)	Cu1—N6	1.974 (2)
C16—H16	0.9300	Cu1—O6	1.9900 (18)
C17—H17	0.9300	Cu1—O1W	2.076 (2)
C18—N3	1.478 (4)	Cu1—O1	2.194 (2)
C18—H18A	0.9700	Cu2—N9	1.963 (2)
C18—H18B	0.9700	Cu2—N4	1.972 (2)
C19—N4	1.325 (4)	Cu2—O2	1.9972 (19)
C19—N3	1.338 (3)	Cu2—O7	2.0458 (19)
C19—H19	0.9300	Cu2—O2W	2.227 (2)
C20—C21	1.348 (5)	N5—H5A	0.8600
C20—N4	1.365 (4)	N5—H5B	0.8600
C20—H20	0.9300	N10—H10A	0.8600
C21—N3	1.352 (4)	N10—H10B	0.8600
C21—H21	0.9300	O3—S1	1.422 (3)
C22—C27	1.404 (4)	O4—S1	1.438 (3)
C22—C23	1.412 (4)	O5—S1	1.436 (3)
C22—C28	1.498 (4)	O8—S2	1.459 (2)
C23—N10	1.359 (4)	O9—S2	1.440 (2)
C23—C24	1.415 (4)	O10—S2	1.460 (2)
C24—C25	1.367 (4)	O1W—H1WA	0.8562
C24—H24	0.9300	O1W—H1WB	0.8523
C25—C26	1.398 (4)	O2W—H2WA	0.8427
C25—H25	0.9300	O2W—H2WB	0.8452
C26—C27	1.370 (4)	O3W—H3WA	0.8513
C26—S2	1.771 (3)	O3W—H3WB	0.8474
C27—H27	0.9300	O4W—H4WA	0.8438
C28—O7	1.246 (3)	O4W—H4WB	0.8444
C28—O6	1.271 (3)	O5W—H5WA	0.8471
C29—N6	1.318 (4)	O5W—H5WB	0.8525
C6—C1—C2	118.8 (2)	C34—C33—C32	122.3 (3)
C6—C1—C7	117.3 (2)	C35—C34—C33	118.5 (3)
C2—C1—C7	123.8 (2)	C35—C34—C39	118.7 (3)
N5—C2—C3	119.1 (3)	C33—C34—C39	122.7 (3)
N5—C2—C1	122.9 (3)	C36—C35—C34	120.7 (3)
C3—C2—C1	117.9 (3)	C36—C35—H35	119.7
C4—C3—C2	121.8 (3)	C34—C35—H35	119.7
C4—C3—H3	119.1	C37—C36—C35	120.0 (4)
C2—C3—H3	119.1	C37—C36—H36	120.0
C3—C4—C5	120.5 (3)	C35—C36—H36	120.0
C3—C4—H4	119.7	C36—C37—C38	120.1 (4)
C5—C4—H4	119.7	C36—C37—H37	120.0
C6—C5—C4	118.8 (3)	C38—C37—H37	120.0
C6—C5—S1	120.2 (2)	C37—C38—C33	121.7 (4)
C4—C5—S1	121.0 (2)	C37—C38—H38	119.2
C5—C6—C1	122.2 (3)	C33—C38—H38	119.2
C5—C6—H6	118.9	N8—C39—C34	111.6 (3)
C1—C6—H6	118.9	N8—C39—H39A	109.3
O1—C7—O2	123.9 (3)	C34—C39—H39A	109.3
O1—C7—C1	118.4 (3)	N8—C39—H39B	109.3
O2—C7—C1	117.6 (2)	C34—C39—H39B	109.3
N1—C8—N2	111.8 (2)	H39A—C39—H39B	108.0
N1—C8—H8	124.1	N9—C40—N8	111.8 (3)
N2—C8—H8	124.1	N9—C40—H40	124.1
C10—C9—N2	107.0 (3)	N8—C40—H40	124.1
C10—C9—H9	126.5	C42—C41—N9	109.7 (3)
N2—C9—H9	126.5	C42—C41—H41	125.2
C9—C10—N1	109.0 (3)	N9—C41—H41	125.2
C9—C10—H10	125.5	N8—C42—C41	106.5 (3)
N1—C10—H10	125.5	N8—C42—H42	126.8
N2—C11—C12	113.6 (2)	C41—C42—H42	126.8
N2—C11—H11A	108.8	N1—Cu1—N6	177.19 (10)
C12—C11—H11A	108.8	N1—Cu1—O6	88.93 (9)
N2—C11—H11B	108.8	N6—Cu1—O6	89.05 (9)
C12—C11—H11B	108.8	N1—Cu1—O1W	89.17 (9)
H11A—C11—H11B	107.7	N6—Cu1—O1W	90.99 (9)
C17—C12—C13	118.6 (3)	O6—Cu1—O1W	137.46 (9)
C17—C12—C11	118.6 (3)	N1—Cu1—O1	90.63 (9)
C13—C12—C11	122.8 (3)	N6—Cu1—O1	92.17 (9)
C14—C13—C12	119.3 (3)	O6—Cu1—O1	130.75 (8)
C14—C13—C18	118.6 (3)	O1W—Cu1—O1	91.77 (8)
C12—C13—C18	122.0 (3)	N9—Cu2—N4	177.69 (10)
C15—C14—C13	121.0 (3)	N9—Cu2—O2	92.40 (9)
C15—C14—H14	119.5	N4—Cu2—O2	89.91 (9)
C13—C14—H14	119.5	N9—Cu2—O7	89.98 (9)
C16—C15—C14	119.8 (3)	N4—Cu2—O7	88.01 (9)
C16—C15—H15	120.1	O2—Cu2—O7	149.89 (9)
C14—C15—H15	120.1	N9—Cu2—O2W	88.55 (9)
C15—C16—C17	120.1 (3)	N4—Cu2—O2W	90.28 (9)
C15—C16—H16	119.9	O2—Cu2—O2W	121.16 (8)
C17—C16—H16	119.9	O7—Cu2—O2W	88.89 (8)
C16—C17—C12	121.1 (3)	C8—N1—C10	105.5 (2)
C16—C17—H17	119.5	C8—N1—Cu1	128.70 (19)
C12—C17—H17	119.5	C10—N1—Cu1	125.8 (2)
N3—C18—C13	110.9 (2)	C8—N2—C9	106.7 (2)
N3—C18—H18A	109.5	C8—N2—C11	128.4 (2)
C13—C18—H18A	109.5	C9—N2—C11	124.7 (2)
N3—C18—H18B	109.5	C19—N3—C21	106.7 (2)
C13—C18—H18B	109.5	C19—N3—C18	126.6 (2)
H18A—C18—H18B	108.0	C21—N3—C18	126.7 (3)
N4—C19—N3	111.5 (2)	C19—N4—C20	105.2 (2)
N4—C19—H19	124.2	C19—N4—Cu2	128.3 (2)
N3—C19—H19	124.2	C20—N4—Cu2	126.3 (2)
C21—C20—N4	109.3 (3)	C2—N5—H5A	120.0
C21—C20—H20	125.3	C2—N5—H5B	120.0
N4—C20—H20	125.3	H5A—N5—H5B	120.0
C20—C21—N3	107.3 (3)	C29—N6—C31	105.2 (2)
C20—C21—H21	126.4	C29—N6—Cu1	124.81 (19)
N3—C21—H21	126.4	C31—N6—Cu1	130.0 (2)
C27—C22—C23	118.8 (2)	C29—N7—C30	107.1 (2)
C27—C22—C28	117.2 (2)	C29—N7—C32	127.2 (3)
C23—C22—C28	124.0 (2)	C30—N7—C32	125.7 (3)
N10—C23—C22	123.0 (2)	C40—N8—C42	106.8 (3)
N10—C23—C24	119.0 (2)	C40—N8—C39	125.7 (3)
C22—C23—C24	117.9 (2)	C42—N8—C39	127.5 (3)
C25—C24—C23	121.6 (3)	C40—N9—C41	105.2 (3)
C25—C24—H24	119.2	C40—N9—Cu2	123.4 (2)
C23—C24—H24	119.2	C41—N9—Cu2	131.0 (2)
C24—C25—C26	120.6 (2)	C23—N10—H10A	120.0
C24—C25—H25	119.7	C23—N10—H10B	120.0
C26—C25—H25	119.7	H10A—N10—H10B	120.0
C27—C26—C25	118.7 (2)	C7—O1—Cu1	158.1 (2)
C27—C26—S2	121.4 (2)	C7—O2—Cu2	113.13 (18)
C25—C26—S2	119.8 (2)	C28—O6—Cu1	126.52 (18)
C26—C27—C22	122.4 (2)	C28—O7—Cu2	148.13 (19)
C26—C27—H27	118.8	Cu1—O1W—H1WA	126.5
C22—C27—H27	118.8	Cu1—O1W—H1WB	124.2
O7—C28—O6	124.8 (2)	H1WA—O1W—H1WB	106.2
O7—C28—C22	116.9 (2)	Cu2—O2W—H2WA	116.5
O6—C28—C22	118.2 (2)	Cu2—O2W—H2WB	129.1
N6—C29—N7	112.1 (3)	H2WA—O2W—H2WB	111.4
N6—C29—H29	124.0	H3WA—O3W—H3WB	106.9
N7—C29—H29	124.0	H4WA—O4W—H4WB	114.3
C31—C30—N7	106.0 (3)	H5WA—O5W—H5WB	107.6
C31—C30—H30	127.0	O3—S1—O5	115.4 (2)
N7—C30—H30	127.0	O3—S1—O4	111.66 (18)
C30—C31—N6	109.6 (3)	O5—S1—O4	110.2 (2)
C30—C31—H31	125.2	O3—S1—C5	106.87 (15)
N6—C31—H31	125.2	O5—S1—C5	105.64 (15)
N7—C32—C33	111.4 (2)	O4—S1—C5	106.38 (14)
N7—C32—H32A	109.3	O9—S2—O8	113.47 (14)
C33—C32—H32A	109.3	O9—S2—O10	112.84 (13)
N7—C32—H32B	109.3	O8—S2—O10	111.32 (12)
C33—C32—H32B	109.3	O9—S2—C26	106.21 (12)
H32A—C32—H32B	108.0	O8—S2—C26	105.93 (12)
C38—C33—C34	119.1 (3)	O10—S2—C26	106.42 (12)
C38—C33—C32	118.6 (3)
C6—C1—C2—N5	−176.7 (3)	C32—C33—C38—C37	−175.8 (3)
C7—C1—C2—N5	5.9 (4)	C35—C34—C39—N8	−98.9 (4)
C6—C1—C2—C3	−0.4 (4)	C33—C34—C39—N8	77.7 (4)
C7—C1—C2—C3	−177.8 (3)	N9—C41—C42—N8	−0.2 (5)
N5—C2—C3—C4	176.9 (3)	N2—C8—N1—C10	1.2 (3)
C1—C2—C3—C4	0.5 (4)	N2—C8—N1—Cu1	−179.29 (18)
C2—C3—C4—C5	−0.2 (5)	C9—C10—N1—C8	−0.6 (4)
C3—C4—C5—C6	−0.1 (4)	C9—C10—N1—Cu1	180.0 (2)
C3—C4—C5—S1	178.0 (2)	N1—C8—N2—C9	−1.5 (3)
C4—C5—C6—C1	0.1 (4)	N1—C8—N2—C11	−176.0 (3)
S1—C5—C6—C1	−178.0 (2)	C10—C9—N2—C8	1.0 (3)
C2—C1—C6—C5	0.2 (4)	C10—C9—N2—C11	175.9 (3)
C7—C1—C6—C5	177.7 (2)	C12—C11—N2—C8	−18.2 (4)
C6—C1—C7—O1	6.0 (4)	C12—C11—N2—C9	168.1 (3)
C2—C1—C7—O1	−176.6 (3)	N4—C19—N3—C21	0.6 (3)
C6—C1—C7—O2	−172.9 (2)	N4—C19—N3—C18	−178.4 (3)
C2—C1—C7—O2	4.5 (4)	C20—C21—N3—C19	−0.4 (4)
N2—C9—C10—N1	−0.3 (4)	C20—C21—N3—C18	178.6 (3)
N2—C11—C12—C17	90.0 (3)	C13—C18—N3—C19	32.3 (4)
N2—C11—C12—C13	−91.6 (3)	C13—C18—N3—C21	−146.5 (3)
C17—C12—C13—C14	−0.2 (4)	N3—C19—N4—C20	−0.6 (3)
C11—C12—C13—C14	−178.7 (3)	N3—C19—N4—Cu2	175.34 (19)
C17—C12—C13—C18	−176.6 (3)	C21—C20—N4—C19	0.3 (4)
C11—C12—C13—C18	4.9 (4)	C21—C20—N4—Cu2	−175.7 (3)
C12—C13—C14—C15	−0.8 (4)	N7—C29—N6—C31	1.3 (3)
C18—C13—C14—C15	175.7 (3)	N7—C29—N6—Cu1	−178.83 (19)
C13—C14—C15—C16	0.8 (5)	C30—C31—N6—C29	−0.8 (4)
C14—C15—C16—C17	0.2 (5)	C30—C31—N6—Cu1	179.3 (2)
C15—C16—C17—C12	−1.3 (5)	N6—C29—N7—C30	−1.2 (3)
C13—C12—C17—C16	1.2 (4)	N6—C29—N7—C32	178.8 (3)
C11—C12—C17—C16	179.8 (3)	C31—C30—N7—C29	0.6 (4)
C14—C13—C18—N3	−102.0 (3)	C31—C30—N7—C32	−179.3 (3)
C12—C13—C18—N3	74.4 (3)	C33—C32—N7—C29	−12.1 (5)
N4—C20—C21—N3	0.1 (4)	C33—C32—N7—C30	167.8 (3)
C27—C22—C23—N10	178.9 (3)	N9—C40—N8—C42	−1.1 (4)
C28—C22—C23—N10	−2.5 (4)	N9—C40—N8—C39	−177.7 (3)
C27—C22—C23—C24	1.0 (4)	C41—C42—N8—C40	0.8 (4)
C28—C22—C23—C24	179.6 (2)	C41—C42—N8—C39	177.3 (3)
N10—C23—C24—C25	−179.5 (3)	C34—C39—N8—C40	49.2 (4)
C22—C23—C24—C25	−1.5 (4)	C34—C39—N8—C42	−126.7 (4)
C23—C24—C25—C26	1.2 (4)	N8—C40—N9—C41	0.9 (4)
C24—C25—C26—C27	−0.4 (4)	N8—C40—N9—Cu2	174.4 (2)
C24—C25—C26—S2	−176.2 (2)	C42—C41—N9—C40	−0.4 (4)
C25—C26—C27—C22	−0.1 (4)	C42—C41—N9—Cu2	−173.2 (3)
S2—C26—C27—C22	175.6 (2)	O2—C7—O1—Cu1	39.2 (7)
C23—C22—C27—C26	−0.2 (4)	C1—C7—O1—Cu1	−139.6 (4)
C28—C22—C27—C26	−178.9 (2)	O1—C7—O2—Cu2	−12.9 (3)
C27—C22—C28—O7	−7.5 (3)	C1—C7—O2—Cu2	165.91 (17)
C23—C22—C28—O7	173.9 (2)	O7—C28—O6—Cu1	1.0 (4)
C27—C22—C28—O6	171.4 (2)	C22—C28—O6—Cu1	−177.83 (16)
C23—C22—C28—O6	−7.2 (4)	O6—C28—O7—Cu2	−9.6 (5)
N7—C30—C31—N6	0.1 (4)	C22—C28—O7—Cu2	169.3 (3)
N7—C32—C33—C38	90.0 (4)	C6—C5—S1—O3	−157.6 (2)
N7—C32—C33—C34	−87.5 (4)	C4—C5—S1—O3	24.3 (3)
C38—C33—C34—C35	−0.6 (4)	C6—C5—S1—O5	79.0 (3)
C32—C33—C34—C35	176.9 (3)	C4—C5—S1—O5	−99.1 (3)
C38—C33—C34—C39	−177.2 (3)	C6—C5—S1—O4	−38.2 (3)
C32—C33—C34—C39	0.3 (4)	C4—C5—S1—O4	143.7 (3)
C33—C34—C35—C36	−0.9 (5)	C27—C26—S2—O9	−114.4 (2)
C39—C34—C35—C36	175.8 (3)	C25—C26—S2—O9	61.3 (3)
C34—C35—C36—C37	1.3 (5)	C27—C26—S2—O8	6.6 (3)
C35—C36—C37—C38	−0.1 (6)	C25—C26—S2—O8	−177.7 (2)
C36—C37—C38—C33	−1.4 (6)	C27—C26—S2—O10	125.1 (2)
C34—C33—C38—C37	1.8 (5)	C25—C26—S2—O10	−59.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5W—H5WB···S2	0.85	3.01	3.708 (3)	141
O5W—H5WB···O8	0.85	1.99	2.818 (3)	164
O5W—H5WA···S1^i	0.85	2.94	3.727 (3)	155
O5W—H5WA···O5^i	0.85	2.27	3.084 (5)	160
O4W—H4WB···O3^ii	0.84	2.11	2.914 (4)	158
O4W—H4WA···O4^i	0.84	2.01	2.826 (4)	162
O3W—H3WB···O10^iii	0.85	2.01	2.857 (3)	174
O3W—H3WA···O8^iv	0.85	1.95	2.788 (3)	169
O2W—H2WB···O3W^v	0.85	1.96	2.789 (3)	168
O2W—H2WA···O5^i	0.84	1.95	2.786 (3)	170
O1W—H1WB···O5W^vi	0.85	1.90	2.727 (3)	162
O1W—H1WA···O4W^vi	0.86	1.96	2.732 (3)	149
N10—H10B···O10^iii	0.86	2.13	2.976 (3)	168
N10—H10A···O6	0.86	2.08	2.705 (3)	129
N5—H5B···O2	0.86	2.06	2.693 (3)	130
C39—H39A···O4^i	0.97	2.65	3.401 (4)	134
C31—H31···O4W^vi	0.93	2.60	3.436 (4)	151
C29—H29···O6	0.93	2.36	2.845 (3)	112
C18—H18A···O9^v	0.97	2.47	3.415 (4)	164
C11—H11B···O10^vii	0.97	2.65	3.176 (4)	114
C9—H9···O3W^iii	0.93	2.54	3.370 (4)	148
C8—H8···O1	0.93	2.61	3.068 (3)	111
O1W—H1WA···O4W^vi	0.86	1.96	2.732 (3)	149
O1W—H1WB···O5W^vi	0.85	1.90	2.727 (3)	162
O2W—H2WA···O5^i	0.84	1.95	2.786 (3)	170
O2W—H2WB···O3W^v	0.85	1.96	2.789 (3)	168
N10—H10B···O10^iii	0.86	2.13	2.976 (3)	168
O3W—H3WA···O8^iv	0.85	1.95	2.788 (3)	169
O3W—H3WB···O10^iii	0.85	2.01	2.857 (3)	174
O4W—H4WA···O4^i	0.84	2.01	2.826 (4)	162
O4W—H4WB···O3^ii	0.84	2.11	2.914 (4)	158
O5W—H5WA···O5^i	0.85	2.27	3.084 (5)	160
O5W—H5WB···O8	0.85	1.99	2.818 (3)	164

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