Bis(2,2′-bipyridine-κ²N,N′)chloro­copper(II) 3-carboxy­benzene­sulfonate trihydrate

In the title compound, [CuCl(C₁₀H₈N₂)₂](C₇H₅O₅S)·3H₂O, the Cu^II ion is coordinated by two 2,2-bipyridine and one chloro ligand in a trigonal–bipyramidal geometry. A hydrogen-bonding network consolidates the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• H-atom completeness 93%
• Disorder in solvent or counterion
• R factor = 0.051
• wR factor = 0.130
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C21
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        >O8
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O8'
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O8'     ..       3.22 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C27 H27 Cl1 Cu1 N4 O8 S1
            Atom count from the _atom_site data:  C27 H25 Cl1 Cu1 N4 O8 S1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C27 H27 Cl Cu N4 O8 S
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         54.00     54.00    0.00
           H         54.00     50.00    4.00
           Cl         2.00      2.00    0.00
           Cu         2.00      2.00    0.00
           N          8.00      8.00    0.00
           O         16.00     16.00    0.00
           S          2.00      2.00    0.00

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(2,2'-bipyridine-κ²N,N')chlorocopper(II) 3-carboxybenzenesulfonate trihydrate

Crystal data

[CuCl(C10H8N2)2](C7H5O5S)·3H2O	Z = 2
Mr = 666.58	F(000) = 686
Triclinic, P1	Dx = 1.541 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4430 (5) Å	Cell parameters from 3862 reflections
b = 11.2269 (7) Å	θ = 2.6–27.5°
c = 15.8025 (10) Å	µ = 0.98 mm^−1
α = 99.098 (1)°	T = 295 K
β = 91.778 (1)°	Plate, blue
γ = 103.189 (1)°	0.38 × 0.26 × 0.24 mm
V = 1436.53 (15) Å^3

Data collection

Bruker APEX area-detector diffractometer	4978 independent reflections
Radiation source: fine-focus sealed tube	4525 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.707, Tmax = 0.798	k = −13→13
7532 measured reflections	l = −18→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 1.4378P] where P = (Fo^2 + 2Fc^2)/3
4978 reflections	(Δ/σ)max < 0.001
389 parameters	Δρmax = 0.38 e Å^−3
12 restraints	Δρmin = −0.53 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	Occ. (<1)
Cu1	0.38850 (5)	0.21714 (4)	0.14509 (3)	0.04131 (15)
S1	1.10226 (11)	0.77161 (8)	0.32784 (6)	0.0472 (2)
Cl1	0.14941 (11)	0.17860 (10)	0.05938 (6)	0.0564 (3)
O1	0.7281 (5)	0.4234 (3)	0.4802 (2)	0.0974 (14)
O2	0.7017 (5)	0.2459 (3)	0.3953 (2)	0.0812 (10)
O3	1.0463 (4)	0.8191 (3)	0.40894 (19)	0.0729 (9)
O4	1.2781 (3)	0.7953 (3)	0.3281 (2)	0.0680 (8)
O5	1.0326 (4)	0.8096 (3)	0.2544 (2)	0.0652 (8)
O6	0.5355 (5)	0.1471 (4)	0.5148 (2)	0.1073 (14)
O7	0.2185 (5)	0.0478 (4)	0.5402 (3)	0.1159 (14)
O8'	0.897 (2)	0.626 (3)	0.0627 (16)	0.112 (8)	0.33 (3)
O8	0.858 (2)	0.5552 (18)	0.0099 (15)	0.178 (8)	0.67 (3)
N1	0.5272 (3)	0.0964 (2)	0.17577 (17)	0.0375 (6)
N2	0.5266 (3)	0.2153 (3)	0.04572 (18)	0.0431 (7)
N3	0.4902 (3)	0.4002 (3)	0.2071 (2)	0.0431 (7)
N4	0.2725 (3)	0.2182 (2)	0.25139 (18)	0.0415 (6)
C1	0.5232 (5)	0.0411 (3)	0.2445 (2)	0.0486 (9)
H1	0.4443	0.0506	0.2831	0.058*
C2	0.6301 (5)	−0.0293 (4)	0.2612 (3)	0.0549 (10)
H2	0.6236	−0.0663	0.3100	0.066*
C3	0.7462 (5)	−0.0439 (3)	0.2046 (3)	0.0542 (9)
H3	0.8205	−0.0907	0.2145	0.065*
C4	0.7518 (4)	0.0120 (3)	0.1323 (2)	0.0471 (8)
H4	0.8296	0.0028	0.0930	0.057*
C5	0.6408 (4)	0.0814 (3)	0.1193 (2)	0.0361 (7)
C6	0.6375 (4)	0.1455 (3)	0.0451 (2)	0.0376 (7)
C7	0.7360 (5)	0.1343 (4)	−0.0224 (2)	0.0485 (9)
H7	0.8109	0.0850	−0.0226	0.058*
C8	0.7217 (5)	0.1974 (4)	−0.0898 (2)	0.0596 (10)
H8	0.7879	0.1919	−0.1355	0.071*
C9	0.6099 (5)	0.2674 (4)	−0.0882 (3)	0.0618 (11)
H9	0.5986	0.3103	−0.1330	0.074*
C10	0.5140 (5)	0.2744 (4)	−0.0203 (3)	0.0577 (10)
H10	0.4371	0.3220	−0.0201	0.069*
C11	0.6003 (4)	0.4898 (3)	0.1793 (3)	0.0525 (9)
H11	0.6423	0.4720	0.1263	0.063*
C12	0.6533 (5)	0.6081 (4)	0.2275 (3)	0.0638 (12)
H12	0.7298	0.6687	0.2071	0.077*
C13	0.5912 (6)	0.6340 (4)	0.3052 (3)	0.0689 (12)
H13	0.6248	0.7128	0.3381	0.083*
C14	0.4790 (5)	0.5435 (3)	0.3346 (3)	0.0572 (10)
H14	0.4353	0.5604	0.3872	0.069*
C15	0.4320 (4)	0.4268 (3)	0.2847 (2)	0.0420 (8)
C16	0.3133 (4)	0.3225 (3)	0.3107 (2)	0.0413 (8)
C17	0.2457 (5)	0.3272 (4)	0.3889 (3)	0.0594 (10)
H17	0.2753	0.3990	0.4299	0.071*
C18	0.1340 (6)	0.2252 (4)	0.4061 (3)	0.0667 (12)
H18	0.0879	0.2276	0.4589	0.080*
C19	0.0914 (5)	0.1205 (4)	0.3451 (3)	0.0583 (10)
H19	0.0157	0.0510	0.3555	0.070*
C20	0.1622 (5)	0.1201 (3)	0.2689 (2)	0.0502 (9)
H20	0.1329	0.0490	0.2273	0.060*
C21	0.7579 (5)	0.3658 (3)	0.4159 (2)	0.0500 (9)
C22	0.8632 (4)	0.4228 (3)	0.3520 (2)	0.0415 (8)
C23	0.9322 (4)	0.5504 (3)	0.3693 (2)	0.0418 (8)
H23	0.9137	0.5974	0.4204	0.050*
C24	1.0278 (4)	0.6071 (3)	0.3109 (2)	0.0418 (8)
C25	1.0575 (5)	0.5358 (4)	0.2355 (2)	0.0522 (9)
H25	1.1225	0.5735	0.1962	0.063*
C26	0.9917 (5)	0.4101 (4)	0.2188 (3)	0.0594 (10)
H26	1.0137	0.3632	0.1685	0.071*
C27	0.8935 (5)	0.3529 (3)	0.2758 (2)	0.0510 (9)
H27	0.8476	0.2680	0.2635	0.061*
H6A	0.4460	0.0950	0.5143	0.080*
H6B	0.5993	0.1470	0.5566	0.080*
H7A	0.1303	0.0728	0.5533	0.080*
H7B	0.1867	−0.0140	0.4968	0.080*
H2A	0.6396	0.2161	0.4347	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0402 (3)	0.0426 (3)	0.0426 (3)	0.01007 (18)	0.01583 (18)	0.00860 (18)
S1	0.0491 (5)	0.0441 (5)	0.0495 (5)	0.0075 (4)	0.0143 (4)	0.0146 (4)
Cl1	0.0427 (5)	0.0717 (6)	0.0525 (5)	0.0163 (4)	0.0061 (4)	−0.0012 (5)
O1	0.161 (4)	0.0465 (17)	0.071 (2)	−0.003 (2)	0.064 (2)	0.0011 (15)
O2	0.119 (3)	0.0418 (15)	0.069 (2)	−0.0069 (16)	0.0334 (19)	0.0012 (14)
O3	0.103 (2)	0.0455 (15)	0.0669 (19)	0.0078 (15)	0.0392 (17)	0.0077 (13)
O4	0.0490 (16)	0.0686 (18)	0.082 (2)	0.0007 (14)	0.0066 (14)	0.0183 (16)
O5	0.0657 (18)	0.0607 (17)	0.076 (2)	0.0145 (14)	0.0087 (15)	0.0326 (15)
O6	0.085 (3)	0.139 (3)	0.074 (2)	−0.036 (2)	−0.0047 (19)	0.039 (2)
O7	0.097 (3)	0.141 (4)	0.106 (3)	0.019 (3)	0.006 (2)	0.021 (3)
O8'	0.117 (10)	0.112 (10)	0.109 (10)	0.017 (6)	0.007 (6)	0.035 (7)
O8	0.219 (12)	0.143 (12)	0.185 (16)	0.031 (10)	0.091 (11)	0.073 (13)
N1	0.0419 (15)	0.0339 (14)	0.0355 (14)	0.0073 (11)	0.0062 (12)	0.0044 (11)
N2	0.0389 (16)	0.0535 (17)	0.0404 (16)	0.0124 (13)	0.0114 (12)	0.0143 (13)
N3	0.0371 (15)	0.0364 (15)	0.0554 (18)	0.0050 (12)	0.0050 (13)	0.0114 (13)
N4	0.0400 (15)	0.0382 (15)	0.0442 (16)	0.0078 (12)	0.0144 (12)	0.0013 (12)
C1	0.056 (2)	0.051 (2)	0.0399 (19)	0.0126 (17)	0.0086 (16)	0.0118 (16)
C2	0.066 (3)	0.053 (2)	0.049 (2)	0.0123 (19)	0.0046 (19)	0.0195 (18)
C3	0.052 (2)	0.045 (2)	0.068 (3)	0.0145 (17)	−0.0005 (19)	0.0130 (18)
C4	0.044 (2)	0.0456 (19)	0.051 (2)	0.0112 (16)	0.0085 (16)	0.0034 (16)
C5	0.0363 (17)	0.0319 (16)	0.0365 (17)	0.0049 (13)	0.0029 (13)	−0.0004 (13)
C6	0.0346 (17)	0.0409 (17)	0.0343 (17)	0.0042 (14)	0.0060 (13)	0.0034 (13)
C7	0.046 (2)	0.056 (2)	0.043 (2)	0.0114 (17)	0.0136 (16)	0.0059 (16)
C8	0.055 (2)	0.078 (3)	0.043 (2)	0.009 (2)	0.0198 (18)	0.0125 (19)
C9	0.054 (2)	0.086 (3)	0.051 (2)	0.011 (2)	0.0116 (18)	0.033 (2)
C10	0.047 (2)	0.077 (3)	0.059 (2)	0.020 (2)	0.0135 (18)	0.033 (2)
C11	0.043 (2)	0.048 (2)	0.068 (3)	0.0065 (17)	0.0040 (18)	0.0200 (18)
C12	0.050 (2)	0.043 (2)	0.097 (4)	−0.0021 (18)	−0.008 (2)	0.028 (2)
C13	0.074 (3)	0.039 (2)	0.087 (3)	0.008 (2)	−0.010 (3)	0.004 (2)
C14	0.059 (2)	0.039 (2)	0.069 (3)	0.0096 (18)	−0.001 (2)	−0.0011 (18)
C15	0.0367 (18)	0.0371 (17)	0.053 (2)	0.0122 (14)	−0.0001 (15)	0.0058 (15)
C16	0.0397 (18)	0.0396 (18)	0.0452 (19)	0.0132 (14)	0.0080 (15)	0.0025 (15)
C17	0.072 (3)	0.053 (2)	0.048 (2)	0.012 (2)	0.016 (2)	−0.0069 (18)
C18	0.078 (3)	0.069 (3)	0.052 (2)	0.012 (2)	0.031 (2)	0.008 (2)
C19	0.059 (2)	0.052 (2)	0.061 (2)	0.0041 (19)	0.029 (2)	0.0112 (19)
C20	0.050 (2)	0.0419 (19)	0.053 (2)	0.0021 (16)	0.0204 (17)	−0.0004 (16)
C21	0.062 (2)	0.042 (2)	0.044 (2)	0.0084 (17)	0.0071 (17)	0.0067 (16)
C22	0.049 (2)	0.0409 (18)	0.0356 (17)	0.0132 (15)	0.0036 (15)	0.0047 (14)
C23	0.050 (2)	0.0413 (18)	0.0347 (17)	0.0123 (15)	0.0067 (15)	0.0042 (14)
C24	0.0407 (18)	0.0413 (18)	0.0454 (19)	0.0108 (15)	0.0050 (15)	0.0111 (15)
C25	0.052 (2)	0.063 (2)	0.045 (2)	0.0173 (19)	0.0198 (17)	0.0097 (17)
C26	0.067 (3)	0.065 (3)	0.048 (2)	0.025 (2)	0.0183 (19)	−0.0020 (19)
C27	0.059 (2)	0.0429 (19)	0.051 (2)	0.0164 (17)	0.0064 (18)	0.0009 (16)

Geometric parameters (Å, º)

Cu1—N1	2.084 (3)	C7—H7	0.9300
Cu1—N2	1.985 (3)	C8—C9	1.358 (6)
Cu1—N3	2.104 (3)	C8—H8	0.9300
Cu1—N4	1.970 (3)	C9—C10	1.368 (5)
Cu1—Cl1	2.3116 (10)	C9—H9	0.9300
S1—O3	1.444 (3)	C10—H10	0.9300
S1—O4	1.447 (3)	C11—C12	1.390 (6)
S1—O5	1.450 (3)	C11—H11	0.9300
S1—C24	1.783 (3)	C12—C13	1.365 (7)
O1—C21	1.182 (4)	C12—H12	0.9300
O2—C21	1.305 (5)	C13—C14	1.372 (6)
O2—H2A	0.8834	C13—H13	0.9300
O6—H6A	0.8425	C14—C15	1.382 (5)
O6—H6B	0.8394	C14—H14	0.9300
O7—H7A	0.8731	C15—C16	1.479 (5)
O7—H7B	0.8812	C16—C17	1.375 (5)
N1—C1	1.332 (4)	C17—C18	1.377 (6)
N1—C5	1.351 (4)	C17—H17	0.9300
N2—C10	1.336 (5)	C18—C19	1.367 (6)
N2—C6	1.350 (4)	C18—H18	0.9300
N3—C11	1.344 (5)	C19—C20	1.360 (5)
N3—C15	1.350 (5)	C19—H19	0.9300
N4—C20	1.342 (4)	C20—H20	0.9300
N4—C16	1.347 (4)	C21—C22	1.490 (5)
C1—C2	1.372 (5)	C22—C27	1.394 (5)
C1—H1	0.9300	C22—C23	1.398 (5)
C2—C3	1.368 (6)	C23—C24	1.380 (5)
C2—H2	0.9300	C23—H23	0.9300
C3—C4	1.384 (5)	C24—C25	1.390 (5)
C3—H3	0.9300	C25—C26	1.373 (6)
C4—C5	1.378 (5)	C25—H25	0.9300
C4—H4	0.9300	C26—C27	1.378 (6)
C5—C6	1.472 (5)	C26—H26	0.9300
C6—C7	1.380 (5)	C27—H27	0.9300
C7—C8	1.386 (5)
N1—Cu1—Cl1	130.39 (8)	C8—C9—H9	120.3
N2—Cu1—Cl1	93.41 (9)	C10—C9—H9	120.3
N3—Cu1—Cl1	118.41 (8)	N2—C10—C9	122.5 (4)
N4—Cu1—Cl1	92.67 (9)	N2—C10—H10	118.8
N2—Cu1—N1	80.22 (11)	C9—C10—H10	118.8
N1—Cu1—N3	111.19 (11)	N3—C11—C12	121.9 (4)
N4—Cu1—N1	94.80 (11)	N3—C11—H11	119.0
N2—Cu1—N3	98.31 (12)	C12—C11—H11	119.0
N4—Cu1—N2	173.78 (12)	C13—C12—C11	118.9 (4)
N4—Cu1—N3	79.93 (11)	C13—C12—H12	120.6
O3—S1—O4	113.1 (2)	C11—C12—H12	120.6
O3—S1—O5	113.8 (2)	C12—C13—C14	119.9 (4)
O4—S1—O5	111.53 (18)	C12—C13—H13	120.1
O3—S1—C24	106.60 (17)	C14—C13—H13	120.1
O4—S1—C24	106.60 (17)	C13—C14—C15	118.9 (4)
O5—S1—C24	104.39 (17)	C13—C14—H14	120.5
C21—O2—H2A	111.2	C15—C14—H14	120.5
H6A—O6—H6B	111.8	N3—C15—C14	122.0 (3)
H7A—O7—H7B	104.9	N3—C15—C16	114.7 (3)
C1—N1—C5	118.4 (3)	C14—C15—C16	123.3 (3)
C1—N1—Cu1	128.5 (2)	N4—C16—C17	120.4 (3)
C5—N1—Cu1	113.0 (2)	N4—C16—C15	115.3 (3)
C10—N2—C6	118.7 (3)	C17—C16—C15	124.3 (3)
C10—N2—Cu1	124.9 (3)	C16—C17—C18	119.7 (4)
C6—N2—Cu1	116.3 (2)	C16—C17—H17	120.1
C11—N3—C15	118.4 (3)	C18—C17—H17	120.1
C11—N3—Cu1	128.8 (3)	C19—C18—C17	119.5 (4)
C15—N3—Cu1	112.9 (2)	C19—C18—H18	120.3
C20—N4—C16	119.1 (3)	C17—C18—H18	120.3
C20—N4—Cu1	123.7 (2)	C20—C19—C18	118.7 (4)
C16—N4—Cu1	117.1 (2)	C20—C19—H19	120.7
N1—C1—C2	123.2 (4)	C18—C19—H19	120.7
N1—C1—H1	118.4	N4—C20—C19	122.6 (3)
C2—C1—H1	118.4	N4—C20—H20	118.7
C3—C2—C1	118.7 (4)	C19—C20—H20	118.7
C3—C2—H2	120.7	O1—C21—O2	122.4 (4)
C1—C2—H2	120.7	O1—C21—C22	123.3 (3)
C2—C3—C4	119.1 (4)	O2—C21—C22	114.3 (3)
C2—C3—H3	120.4	C27—C22—C23	119.4 (3)
C4—C3—H3	120.4	C27—C22—C21	122.0 (3)
C5—C4—C3	119.3 (3)	C23—C22—C21	118.6 (3)
C5—C4—H4	120.3	C24—C23—C22	120.3 (3)
C3—C4—H4	120.3	C24—C23—H23	119.8
N1—C5—C4	121.3 (3)	C22—C23—H23	119.8
N1—C5—C6	115.1 (3)	C23—C24—C25	119.5 (3)
C4—C5—C6	123.6 (3)	C23—C24—S1	120.7 (3)
N2—C6—C7	121.1 (3)	C25—C24—S1	119.7 (3)
N2—C6—C5	115.2 (3)	C26—C25—C24	120.5 (3)
C7—C6—C5	123.6 (3)	C26—C25—H25	119.8
C6—C7—C8	119.1 (4)	C24—C25—H25	119.8
C6—C7—H7	120.5	C25—C26—C27	120.6 (3)
C8—C7—H7	120.5	C25—C26—H26	119.7
C9—C8—C7	119.2 (4)	C27—C26—H26	119.7
C9—C8—H8	120.4	C26—C27—C22	119.8 (3)
C7—C8—H8	120.4	C26—C27—H27	120.1
C8—C9—C10	119.4 (4)	C22—C27—H27	120.1
N4—Cu1—N1—C1	2.1 (3)	C7—C8—C9—C10	0.1 (7)
N2—Cu1—N1—C1	178.4 (3)	C6—N2—C10—C9	−0.4 (6)
N3—Cu1—N1—C1	83.2 (3)	Cu1—N2—C10—C9	−178.4 (3)
Cl1—Cu1—N1—C1	−95.5 (3)	C8—C9—C10—N2	0.5 (7)
N4—Cu1—N1—C5	−173.4 (2)	C15—N3—C11—C12	−0.9 (5)
N2—Cu1—N1—C5	2.8 (2)	Cu1—N3—C11—C12	178.5 (3)
N3—Cu1—N1—C5	−92.4 (2)	N3—C11—C12—C13	−0.2 (6)
Cl1—Cu1—N1—C5	88.9 (2)	C11—C12—C13—C14	0.3 (6)
N1—Cu1—N2—C10	176.9 (3)	C12—C13—C14—C15	0.5 (6)
N3—Cu1—N2—C10	−72.9 (3)	C11—N3—C15—C14	1.8 (5)
Cl1—Cu1—N2—C10	46.4 (3)	Cu1—N3—C15—C14	−177.7 (3)
N1—Cu1—N2—C6	−1.2 (2)	C11—N3—C15—C16	−179.2 (3)
N3—Cu1—N2—C6	109.0 (2)	Cu1—N3—C15—C16	1.3 (4)
Cl1—Cu1—N2—C6	−131.6 (2)	C13—C14—C15—N3	−1.6 (6)
N4—Cu1—N3—C11	−178.6 (3)	C13—C14—C15—C16	179.4 (4)
N2—Cu1—N3—C11	7.4 (3)	C20—N4—C16—C17	1.5 (5)
N1—Cu1—N3—C11	90.1 (3)	Cu1—N4—C16—C17	−175.5 (3)
Cl1—Cu1—N3—C11	−91.1 (3)	C20—N4—C16—C15	−178.3 (3)
N4—Cu1—N3—C15	0.8 (2)	Cu1—N4—C16—C15	4.6 (4)
N2—Cu1—N3—C15	−173.1 (2)	N3—C15—C16—N4	−3.8 (4)
N1—Cu1—N3—C15	−90.5 (2)	C14—C15—C16—N4	175.2 (3)
Cl1—Cu1—N3—C15	88.4 (2)	N3—C15—C16—C17	176.3 (3)
N1—Cu1—N4—C20	−69.3 (3)	C14—C15—C16—C17	−4.7 (6)
N3—Cu1—N4—C20	−180.0 (3)	N4—C16—C17—C18	−0.9 (6)
Cl1—Cu1—N4—C20	61.6 (3)	C15—C16—C17—C18	179.0 (4)
N1—Cu1—N4—C16	107.7 (3)	C16—C17—C18—C19	−0.1 (7)
N3—Cu1—N4—C16	−3.0 (2)	C17—C18—C19—C20	0.4 (7)
Cl1—Cu1—N4—C16	−121.4 (2)	C16—N4—C20—C19	−1.3 (6)
C5—N1—C1—C2	0.7 (5)	Cu1—N4—C20—C19	175.6 (3)
Cu1—N1—C1—C2	−174.7 (3)	C18—C19—C20—N4	0.3 (7)
N1—C1—C2—C3	−0.2 (6)	O1—C21—C22—C27	−178.6 (4)
C1—C2—C3—C4	−0.3 (6)	O2—C21—C22—C27	1.8 (6)
C2—C3—C4—C5	0.3 (6)	O1—C21—C22—C23	0.9 (6)
C1—N1—C5—C4	−0.8 (5)	O2—C21—C22—C23	−178.7 (4)
Cu1—N1—C5—C4	175.3 (2)	C27—C22—C23—C24	0.8 (5)
C1—N1—C5—C6	−179.9 (3)	C21—C22—C23—C24	−178.7 (3)
Cu1—N1—C5—C6	−3.9 (3)	C22—C23—C24—C25	−1.3 (5)
C3—C4—C5—N1	0.3 (5)	C22—C23—C24—S1	174.6 (3)
C3—C4—C5—C6	179.4 (3)	O3—S1—C24—C23	1.6 (4)
C10—N2—C6—C7	−0.4 (5)	O4—S1—C24—C23	122.7 (3)
Cu1—N2—C6—C7	177.8 (3)	O5—S1—C24—C23	−119.1 (3)
C10—N2—C6—C5	−178.7 (3)	O3—S1—C24—C25	177.5 (3)
Cu1—N2—C6—C5	−0.5 (4)	O4—S1—C24—C25	−61.4 (3)
N1—C5—C6—N2	3.0 (4)	O5—S1—C24—C25	56.7 (3)
C4—C5—C6—N2	−176.1 (3)	C23—C24—C25—C26	0.4 (6)
N1—C5—C6—C7	−175.3 (3)	S1—C24—C25—C26	−175.5 (3)
C4—C5—C6—C7	5.6 (5)	C24—C25—C26—C27	0.8 (6)
N2—C6—C7—C8	1.0 (5)	C25—C26—C27—C22	−1.3 (6)
C5—C6—C7—C8	179.2 (3)	C23—C22—C27—C26	0.4 (6)
C6—C7—C8—C9	−0.8 (6)	C21—C22—C27—C26	180.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	0.84	1.95	2.723 (6)	153
O6—H6B···O4^i	0.84	2.00	2.801 (5)	158
O7—H7A···O3^ii	0.87	2.17	3.022 (6)	165
O7—H7B···O3^iii	0.88	2.21	3.071 (6)	164
O2—H2A···O6	0.88	1.74	2.624 (5)	173
C3—H3···O5^iv	0.93	2.43	3.358 (5)	173
C8—H8···O5^v	0.93	2.45	3.379 (5)	177

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