Bis(2,2'-bi­pyridine)(3-carboxy-4-hydroxy­benzene­sulfonato)copper(II) 3-carboxy-4-hydroxy­benzene­sulfonate

The Cu atom in the title compound, [Cu(C₇H₅O₆S)(C₁₀H₈N₂)](C₇H₅O₆S), is chelated by the two N-heterocycles and is covalently bonded to the sulfonate O atom of the sulfosalicyl­ate ion in a trigonal-bipyramidal geometry. The uncoordinated sulfosalicyl­ate anion interacts with adjacent anions, forming a linear hydrogen-bonded chain; the mononuclear cations are appended to the chain by hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.067
• wR factor = 0.147
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.407     0.885
            Tmin' and Tmax expected:      0.762     0.883
            RR' =      0.533
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.53

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.11
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O6   -H6O     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O10  -H10O    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.850(10) ......       3.00 su-Rat
              O6   -H6O     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O10  -H10O    1.555   1.555

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

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

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(2,2'-bipyridine)(3-carboxy-4-hydroxybenzenesulfonato)copper(II) 3-carboxy-4-hydroxybenzenesulfonate

Crystal data

[Cu(C7H5O6S)(C10H8N2)](C7H5O6S)	Z = 2
Mr = 810.25	F(000) = 830
Triclinic, P1	Dx = 1.575 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.343 (2) Å	Cell parameters from 12885 reflections
b = 12.302 (3) Å	θ = 3.1–27.7°
c = 17.540 (4) Å	µ = 0.83 mm^−1
α = 98.82 (3)°	T = 295 K
β = 102.77 (3)°	Prism, blue
γ = 97.70 (3)°	0.32 × 0.24 × 0.15 mm
V = 1708.4 (6) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	7633 independent reflections
Radiation source: fine-focus sealed tube	4117 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
ω scans	θmax = 27.7°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.407, Tmax = 0.885	k = −15→15
15414 measured reflections	l = −22→22

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)] = 0.067	Hydrogen site location: difmap (O-H) and geom (others)
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0627P)^2] where P = (Fo^2 + 2Fc^2)/3
7633 reflections	(Δ/σ)max = 0.001
494 parameters	Δρmax = 0.46 e Å^−3
4 restraints	Δρmin = −0.42 e Å^−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.38848 (7)	0.70540 (4)	0.88117 (3)	0.04094 (18)
S1	0.7615 (2)	0.6868 (1)	0.90842 (7)	0.0451 (3)
S2	0.7099 (1)	0.03617 (9)	0.67018 (6)	0.0357 (3)
O1	0.6436 (4)	0.7671 (3)	0.9004 (2)	0.048 (1)
O2	0.9203 (4)	0.7405 (3)	0.9611 (2)	0.062 (1)
O3	0.6854 (5)	0.5812 (3)	0.9256 (2)	0.061 (1)
O4	0.8897 (6)	0.5837 (4)	0.5925 (2)	0.078 (1)
O5	0.7682 (5)	0.3742 (3)	0.5886 (2)	0.077 (1)
O6	0.6608 (5)	0.3270 (3)	0.6869 (2)	0.060 (1)
O7	0.6163 (4)	0.1133 (2)	0.6306 (2)	0.050 (1)
O8	0.5972 (4)	−0.0466 (3)	0.6956 (2)	0.047 (1)
O9	0.8510 (4)	0.0924 (3)	0.7333 (2)	0.058 (1)
O10	0.9681 (4)	−0.2395 (3)	0.4372 (2)	0.057 (1)
O11	1.2656 (4)	−0.1581 (3)	0.5323 (2)	0.053 (1)
O12	1.2810 (4)	−0.0460 (3)	0.6468 (2)	0.057 (1)
N1	0.2333 (4)	0.5530 (3)	0.8608 (2)	0.044 (1)
N2	0.3724 (4)	0.6583 (3)	0.7674 (2)	0.040 (1)
N3	0.4043 (4)	0.7429 (3)	0.9962 (2)	0.038 (1)
N4	0.3043 (4)	0.8612 (3)	0.8873 (2)	0.040 (1)
C1	0.1591 (6)	0.5065 (5)	0.9117 (3)	0.057 (1)
C2	0.0619 (6)	0.3993 (5)	0.8915 (3)	0.065 (2)
C3	0.0404 (7)	0.3392 (4)	0.8187 (4)	0.065 (2)
C4	0.1133 (6)	0.3846 (4)	0.7641 (3)	0.054 (1)
C5	0.2072 (5)	0.4931 (3)	0.7871 (3)	0.038 (1)
C6	0.2871 (5)	0.5530 (4)	0.7340 (3)	0.042 (1)
C7	0.2768 (7)	0.5060 (5)	0.6560 (3)	0.062 (1)
C8	0.3544 (7)	0.5718 (5)	0.6120 (3)	0.066 (2)
C9	0.4408 (7)	0.6794 (5)	0.6460 (3)	0.059 (1)
C10	0.4484 (6)	0.7183 (4)	0.7234 (3)	0.048 (1)
C11	0.4685 (6)	0.6811 (4)	1.0487 (3)	0.050 (1)
C12	0.4745 (6)	0.7080 (4)	1.1274 (3)	0.056 (1)
C13	0.4126 (7)	0.8019 (5)	1.1538 (3)	0.065 (2)
C14	0.3501 (6)	0.8674 (4)	1.1006 (3)	0.058 (1)
C15	0.3478 (5)	0.8370 (4)	1.0220 (3)	0.040 (1)
C16	0.2874 (5)	0.9015 (4)	0.9593 (3)	0.040 (1)
C17	0.2225 (6)	0.9994 (4)	0.9741 (3)	0.055 (1)
C18	0.1724 (6)	1.0565 (4)	0.9133 (3)	0.063 (1)
C19	0.1926 (7)	1.0156 (4)	0.8402 (3)	0.061 (1)
C20	0.2561 (6)	0.9176 (4)	0.8286 (3)	0.051 (1)
C21	0.7804 (5)	0.5168 (4)	0.6963 (3)	0.041 (1)
C22	0.8565 (6)	0.6031 (4)	0.6643 (3)	0.050 (1)
C23	0.9009 (6)	0.7135 (4)	0.7070 (3)	0.058 (1)
C24	0.8718 (6)	0.7389 (4)	0.7807 (3)	0.056 (1)
C25	0.7973 (5)	0.6536 (4)	0.8137 (3)	0.039 (1)
C26	0.7535 (5)	0.5446 (4)	0.7714 (3)	0.039 (1)
C27	0.7351 (6)	0.4009 (4)	0.6519 (3)	0.050 (1)
C28	1.0207 (5)	−0.1062 (3)	0.5592 (2)	0.031 (1)
C29	0.9152 (5)	−0.1731 (4)	0.4909 (3)	0.039 (1)
C30	0.7440 (6)	−0.1734 (4)	0.4767 (3)	0.050 (1)
C31	0.6806 (5)	−0.1099 (4)	0.5297 (3)	0.042 (1)
C32	0.7858 (5)	−0.0426 (3)	0.5982 (2)	0.032 (1)
C33	0.9550 (5)	−0.0401 (3)	0.6118 (2)	0.032 (1)
C34	1.2000 (5)	−0.1058 (4)	0.5767 (3)	0.039 (1)
H4o	0.867 (7)	0.513 (1)	0.583 (3)	0.07 (2)*
H6o	0.648 (6)	0.261 (2)	0.660 (3)	0.068 (17)*
H10o	1.074 (2)	−0.227 (5)	0.453 (3)	0.09 (2)*
H12o	1.382 (2)	−0.055 (4)	0.654 (3)	0.054 (15)*
H1	0.1729	0.5474	0.9626	0.069*
H2	0.0129	0.3703	0.9285	0.078*
H3	−0.0228	0.2677	0.8047	0.078*
H4	0.1002	0.3438	0.7132	0.065*
H7	0.2206	0.4337	0.6338	0.074*
H8	0.3483	0.5434	0.5589	0.079*
H9	0.4918	0.7233	0.6164	0.070*
H10	0.5085	0.7892	0.7471	0.058*
H11	0.5099	0.6182	1.0304	0.060*
H12	0.5191	0.6644	1.1627	0.067*
H13	0.4131	0.8211	1.2073	0.078*
H14	0.3102	0.9313	1.1182	0.070*
H17	0.2129	1.0264	1.0251	0.066*
H18	0.1264	1.1207	0.9222	0.075*
H19	0.1641	1.0530	0.7983	0.073*
H20	0.2660	0.8894	0.7779	0.061*
H23	0.9502	0.7693	0.6851	0.070*
H24	0.9008	0.8120	0.8089	0.067*
H26	0.7052	0.4891	0.7940	0.047*
H30	0.6725	−0.2173	0.4308	0.060*
H31	0.5660	−0.1116	0.5199	0.051*
H33	1.0262	0.0064	0.6568	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0582 (4)	0.0299 (3)	0.0329 (3)	0.0046 (3)	0.0147 (3)	−0.0022 (2)
S1	0.0550 (7)	0.0404 (7)	0.0379 (6)	0.0040 (6)	0.0166 (6)	−0.0021 (5)
S2	0.0300 (5)	0.0352 (6)	0.0384 (6)	0.0089 (5)	0.0075 (5)	−0.0056 (5)
O1	0.049 (2)	0.042 (2)	0.049 (2)	0.011 (2)	0.016 (2)	−0.008 (2)
O2	0.050 (2)	0.074 (3)	0.048 (2)	0.004 (2)	−0.002 (2)	−0.007 (2)
O3	0.094 (3)	0.041 (2)	0.053 (2)	0.002 (2)	0.037 (2)	0.004 (2)
O4	0.106 (3)	0.086 (4)	0.061 (3)	0.026 (3)	0.051 (2)	0.023 (2)
O5	0.120 (3)	0.069 (3)	0.049 (2)	0.028 (2)	0.035 (2)	−0.002 (2)
O6	0.089 (3)	0.036 (2)	0.054 (2)	0.017 (2)	0.020 (2)	−0.006 (2)
O7	0.055 (2)	0.040 (2)	0.055 (2)	0.021 (2)	0.012 (2)	0.001 (2)
O8	0.044 (2)	0.050 (2)	0.051 (2)	0.010 (2)	0.021 (2)	0.008 (2)
O9	0.036 (2)	0.069 (2)	0.053 (2)	0.010 (2)	0.003 (2)	−0.028 (2)
O10	0.047 (2)	0.068 (2)	0.050 (2)	0.016 (2)	0.012 (2)	−0.017 (2)
O11	0.042 (2)	0.067 (2)	0.048 (2)	0.017 (2)	0.016 (2)	−0.006 (2)
O12	0.027 (2)	0.086 (3)	0.049 (2)	0.009 (2)	0.010 (2)	−0.013 (2)
N1	0.049 (2)	0.040 (2)	0.040 (2)	0.006 (2)	0.007 (2)	0.006 (2)
N2	0.051 (2)	0.035 (2)	0.033 (2)	0.010 (2)	0.009 (2)	0.006 (2)
N3	0.049 (2)	0.033 (2)	0.032 (2)	0.001 (2)	0.017 (2)	−0.001 (2)
N4	0.046 (2)	0.035 (2)	0.034 (2)	0.005 (2)	0.011 (2)	−0.002 (2)
C1	0.062 (3)	0.063 (3)	0.046 (3)	−0.002 (3)	0.017 (3)	0.010 (3)
C2	0.060 (3)	0.060 (4)	0.062 (4)	−0.015 (3)	−0.002 (3)	0.022 (3)
C3	0.058 (3)	0.040 (3)	0.082 (4)	−0.005 (3)	−0.011 (3)	0.017 (3)
C4	0.053 (3)	0.038 (3)	0.057 (3)	0.009 (2)	−0.009 (3)	−0.004 (2)
C5	0.041 (2)	0.030 (2)	0.039 (3)	0.007 (2)	0.003 (2)	0.000 (2)
C6	0.045 (3)	0.040 (3)	0.035 (3)	0.014 (2)	0.002 (2)	−0.005 (2)
C7	0.068 (3)	0.063 (4)	0.044 (3)	0.011 (3)	0.004 (3)	−0.011 (3)
C8	0.079 (4)	0.086 (4)	0.028 (3)	0.021 (3)	0.008 (3)	−0.002 (3)
C9	0.075 (4)	0.068 (4)	0.040 (3)	0.027 (3)	0.014 (3)	0.017 (3)
C10	0.058 (3)	0.047 (3)	0.040 (3)	0.016 (2)	0.011 (2)	0.006 (2)
C11	0.071 (3)	0.037 (3)	0.042 (3)	0.008 (2)	0.018 (3)	0.003 (2)
C12	0.073 (3)	0.055 (3)	0.040 (3)	0.006 (3)	0.017 (3)	0.013 (2)
C13	0.081 (4)	0.084 (4)	0.034 (3)	0.021 (3)	0.022 (3)	0.003 (3)
C14	0.069 (3)	0.061 (3)	0.047 (3)	0.020 (3)	0.026 (3)	−0.009 (3)
C15	0.039 (2)	0.042 (3)	0.034 (2)	0.004 (2)	0.009 (2)	−0.008 (2)
C16	0.038 (2)	0.032 (2)	0.044 (3)	0.002 (2)	0.011 (2)	−0.004 (2)
C17	0.068 (3)	0.042 (3)	0.051 (3)	0.013 (3)	0.016 (3)	−0.010 (2)
C18	0.063 (3)	0.049 (3)	0.068 (4)	0.023 (3)	0.002 (3)	−0.003 (3)
C19	0.077 (4)	0.040 (3)	0.059 (4)	0.018 (3)	0.000 (3)	0.008 (3)
C20	0.063 (3)	0.041 (3)	0.044 (3)	0.012 (2)	0.006 (3)	0.001 (2)
C21	0.048 (3)	0.038 (3)	0.040 (3)	0.018 (2)	0.014 (2)	0.007 (2)
C22	0.054 (3)	0.061 (3)	0.047 (3)	0.023 (3)	0.026 (3)	0.018 (3)
C23	0.071 (4)	0.051 (3)	0.064 (4)	0.010 (3)	0.035 (3)	0.020 (3)
C24	0.067 (3)	0.036 (3)	0.066 (4)	0.003 (3)	0.026 (3)	0.006 (3)
C25	0.043 (2)	0.035 (2)	0.039 (3)	0.007 (2)	0.012 (2)	0.006 (2)
C26	0.045 (3)	0.037 (2)	0.038 (2)	0.013 (2)	0.012 (2)	0.009 (2)
C27	0.069 (3)	0.047 (3)	0.033 (3)	0.021 (3)	0.009 (2)	0.000 (2)
C28	0.031 (2)	0.033 (2)	0.031 (2)	0.008 (2)	0.009 (2)	0.004 (2)
C29	0.039 (2)	0.038 (2)	0.039 (3)	0.010 (2)	0.016 (2)	−0.005 (2)
C30	0.038 (3)	0.058 (3)	0.043 (3)	0.006 (2)	0.004 (2)	−0.010 (2)
C31	0.028 (2)	0.049 (3)	0.043 (3)	0.008 (2)	0.005 (2)	−0.006 (2)
C32	0.031 (2)	0.034 (2)	0.030 (2)	0.006 (2)	0.008 (2)	−0.003 (2)
C33	0.033 (2)	0.029 (2)	0.033 (2)	0.003 (2)	0.008 (2)	0.003 (2)
C34	0.036 (2)	0.047 (3)	0.034 (2)	0.011 (2)	0.011 (2)	0.004 (2)

Geometric parameters (Å, º)

Cu1—O1	2.096 (3)	C18—C19	1.359 (7)
Cu1—N1	2.064 (4)	C19—C20	1.385 (7)
Cu1—N2	1.960 (4)	C21—C26	1.383 (6)
Cu1—N3	1.970 (3)	C21—C22	1.417 (6)
Cu1—N4	2.123 (4)	C21—C27	1.472 (6)
S1—O2	1.443 (3)	C22—C23	1.405 (7)
S1—O3	1.470 (3)	C23—C24	1.364 (7)
S1—O1	1.485 (3)	C24—C25	1.412 (6)
S1—C25	1.748 (4)	C25—C26	1.389 (6)
S2—O9	1.436 (3)	C28—C29	1.388 (6)
S2—O7	1.468 (3)	C28—C33	1.387 (5)
S2—O8	1.479 (3)	C28—C34	1.458 (5)
S2—C32	1.754 (4)	C29—C30	1.394 (6)
O4—C22	1.341 (6)	C30—C31	1.364 (6)
O5—C27	1.211 (5)	C31—C32	1.391 (6)
O6—C27	1.332 (6)	C32—C33	1.374 (5)
O10—C29	1.338 (5)	O4—H4o	0.85 (1)
O11—C34	1.205 (5)	O6—H6o	0.85 (1)
O12—C34	1.315 (5)	O10—H10o	0.85 (1)
N1—C5	1.342 (5)	O12—H12o	0.85 (1)
N1—C1	1.346 (5)	C1—H1	0.93
N2—C10	1.344 (5)	C2—H2	0.93
N2—C6	1.365 (6)	C3—H3	0.93
N3—C11	1.348 (5)	C4—H4	0.93
N3—C15	1.359 (5)	C7—H7	0.93
N4—C16	1.328 (5)	C8—H8	0.93
N4—C20	1.347 (5)	C9—H9	0.93
C1—C2	1.402 (7)	C10—H10	0.93
C2—C3	1.335 (8)	C11—H11	0.93
C3—C4	1.389 (7)	C12—H12	0.93
C4—C5	1.404 (6)	C13—H13	0.93
C5—C6	1.486 (6)	C14—H14	0.93
C6—C7	1.381 (6)	C17—H17	0.93
C7—C8	1.394 (7)	C18—H18	0.93
C8—C9	1.393 (8)	C19—H19	0.93
C9—C10	1.353 (6)	C20—H20	0.93
C11—C12	1.357 (6)	C23—H23	0.93
C12—C13	1.385 (7)	C24—H24	0.93
C13—C14	1.385 (7)	C26—H26	0.93
C14—C15	1.368 (6)	C30—H30	0.93
C15—C16	1.491 (6)	C31—H31	0.93
C16—C17	1.397 (6)	C33—H33	0.93
C17—C18	1.384 (7)
O1—Cu1—N1	138.3 (1)	C26—C25—C24	120.1 (4)
O1—Cu1—N2	90.1 (1)	C26—C25—S1	120.5 (3)
O1—Cu1—N3	90.7 (1)	C24—C25—S1	119.4 (4)
O1—Cu1—N4	97.6 (1)	C21—C26—C25	121.3 (4)
N1—Cu1—N2	80.7 (2)	O5—C27—O6	122.3 (5)
N1—Cu1—N3	96.4 (2)	O5—C27—C21	121.7 (5)
N1—Cu1—N4	124.1 (1)	O6—C27—C21	115.9 (4)
N2—Cu1—N3	176.4 (2)	C29—C28—C33	119.8 (4)
N2—Cu1—N4	103.4 (1)	C29—C28—C34	120.5 (4)
N3—Cu1—N4	80.0 (1)	C33—C28—C34	119.7 (4)
O2—S1—O3	116.3 (2)	O10—C29—C28	123.7 (4)
O2—S1—O1	110.5 (2)	O10—C29—C30	117.2 (4)
O3—S1—O1	111.9 (2)	C28—C29—C30	119.1 (4)
O2—S1—C25	106.4 (2)	C31—C30—C29	120.6 (4)
O3—S1—C25	105.9 (2)	C30—C31—C32	120.5 (4)
O1—S1—C25	104.9 (2)	C33—C32—C31	119.3 (4)
O9—S2—O7	113.0 (2)	C33—C32—S2	118.4 (3)
O9—S2—O8	113.1 (2)	C31—C32—S2	122.3 (3)
O7—S2—O8	110.8 (2)	C32—C33—C28	120.7 (4)
O9—S2—C32	107.5 (2)	O11—C34—O12	123.7 (4)
O7—S2—C32	107.2 (2)	O11—C34—C28	123.0 (4)
O8—S2—C32	104.8 (2)	O12—C34—C28	113.2 (4)
S1—O1—Cu1	118.2 (2)	C22—O4—H4o	99 (4)
C5—N1—C1	117.0 (4)	C27—O6—H6o	111 (3)
C5—N1—Cu1	114.4 (3)	C29—O10—H10o	105 (4)
C1—N1—Cu1	128.6 (3)	C34—O12—H12o	107 (3)
C10—N2—C6	119.4 (4)	N1—C1—H1	118.5
C10—N2—Cu1	124.8 (3)	C2—C1—H1	118.5
C6—N2—Cu1	115.6 (3)	C3—C2—H2	120.3
C11—N3—C15	120.0 (4)	C1—C2—H2	120.3
C11—N3—Cu1	123.4 (3)	C2—C3—H3	120.3
C15—N3—Cu1	116.6 (3)	C4—C3—H3	120.3
C16—N4—C20	117.8 (4)	C3—C4—H4	120.6
C16—N4—Cu1	112.7 (3)	C5—C4—H4	120.6
C20—N4—Cu1	129.3 (3)	C6—C7—H7	121.5
N1—C1—C2	123.1 (5)	C8—C7—H7	121.5
C3—C2—C1	119.4 (5)	C9—C8—H8	119.4
C2—C3—C4	119.3 (5)	C7—C8—H8	119.4
C3—C4—C5	118.8 (5)	C10—C9—H9	121.0
N1—C5—C4	122.3 (4)	C8—C9—H9	121.0
N1—C5—C6	113.3 (4)	N2—C10—H10	118.7
C4—C5—C6	124.5 (4)	C9—C10—H10	118.7
N2—C6—C7	121.7 (4)	N3—C11—H11	119.1
N2—C6—C5	115.6 (4)	C12—C11—H11	119.1
C7—C6—C5	122.7 (4)	C11—C12—H12	120.7
C6—C7—C8	117.1 (5)	C13—C12—H12	120.7
C9—C8—C7	121.2 (5)	C12—C13—H13	120.0
C10—C9—C8	118.1 (5)	C14—C13—H13	120.0
N2—C10—C9	122.6 (5)	C15—C14—H14	120.4
N3—C11—C12	121.9 (5)	C13—C14—H14	120.4
C11—C12—C13	118.5 (5)	C18—C17—H17	119.8
C12—C13—C14	119.9 (5)	C16—C17—H17	119.8
C15—C14—C13	119.3 (5)	C19—C18—H18	121.1
N3—C15—C14	120.3 (4)	C17—C18—H18	121.1
N3—C15—C16	115.3 (4)	C18—C19—H19	120.3
C14—C15—C16	124.5 (4)	C20—C19—H19	120.3
N4—C16—C17	121.4 (4)	N4—C20—H20	118.4
N4—C16—C15	115.0 (4)	C19—C20—H20	118.4
C17—C16—C15	123.5 (4)	C24—C23—H23	120.0
C18—C17—C16	120.4 (5)	C22—C23—H23	120.0
C19—C18—C17	117.8 (5)	C23—C24—H24	120.2
C18—C19—C20	119.4 (5)	C25—C24—H24	120.2
N4—C20—C19	123.2 (5)	C21—C26—H26	119.3
C26—C21—C22	117.9 (4)	C25—C26—H26	119.3
C26—C21—C27	121.2 (4)	C31—C30—H30	119.7
C22—C21—C27	121.0 (4)	C29—C30—H30	119.7
O4—C22—C23	117.0 (5)	C30—C31—H31	119.7
O4—C22—C21	122.0 (5)	C32—C31—H31	119.7
C23—C22—C21	120.9 (4)	C32—C33—H33	119.6
C24—C23—C22	120.1 (5)	C28—C33—H33	119.6
C23—C24—C25	119.7 (5)
O2—S1—O1—Cu1	−148.7 (2)	Cu1—N3—C15—C14	178.2 (4)
O3—S1—O1—Cu1	−17.4 (3)	C11—N3—C15—C16	177.1 (4)
C25—S1—O1—Cu1	97.0 (2)	Cu1—N3—C15—C16	−2.3 (5)
N2—Cu1—O1—S1	−81.7 (2)	C13—C14—C15—N3	0.8 (7)
N3—Cu1—O1—S1	94.8 (2)	C13—C14—C15—C16	−178.6 (5)
N1—Cu1—O1—S1	−5.6 (3)	C20—N4—C16—C17	−0.2 (6)
N4—Cu1—O1—S1	174.8 (2)	Cu1—N4—C16—C17	−175.6 (3)
N2—Cu1—N1—C5	5.0 (3)	C20—N4—C16—C15	−178.2 (4)
N3—Cu1—N1—C5	−172.8 (3)	Cu1—N4—C16—C15	6.4 (5)
O1—Cu1—N1—C5	−74.6 (4)	N3—C15—C16—N4	−3.1 (6)
N4—Cu1—N1—C5	105.0 (3)	C14—C15—C16—N4	176.4 (4)
N2—Cu1—N1—C1	−176.2 (4)	N3—C15—C16—C17	179.0 (4)
N3—Cu1—N1—C1	5.9 (4)	C14—C15—C16—C17	−1.6 (7)
O1—Cu1—N1—C1	104.2 (4)	N4—C16—C17—C18	0.6 (7)
N4—Cu1—N1—C1	−76.2 (4)	C15—C16—C17—C18	178.4 (4)
N1—Cu1—N2—C10	179.8 (4)	C16—C17—C18—C19	−1.6 (8)
O1—Cu1—N2—C10	−41.0 (4)	C17—C18—C19—C20	2.3 (8)
N4—Cu1—N2—C10	56.8 (4)	C16—N4—C20—C19	0.9 (7)
N1—Cu1—N2—C6	−5.3 (3)	Cu1—N4—C20—C19	175.4 (4)
O1—Cu1—N2—C6	133.9 (3)	C18—C19—C20—N4	−2.0 (8)
N4—Cu1—N2—C6	−128.3 (3)	C26—C21—C22—O4	179.0 (4)
N1—Cu1—N3—C11	61.4 (4)	C27—C21—C22—O4	0.4 (7)
O1—Cu1—N3—C11	−77.4 (4)	C26—C21—C22—C23	−0.9 (7)
N4—Cu1—N3—C11	−175.0 (4)	C27—C21—C22—C23	−179.5 (5)
N1—Cu1—N3—C15	−119.2 (3)	O4—C22—C23—C24	−179.5 (5)
O1—Cu1—N3—C15	102.0 (3)	C21—C22—C23—C24	0.4 (8)
N4—Cu1—N3—C15	4.4 (3)	C22—C23—C24—C25	0.2 (8)
N2—Cu1—N4—C16	172.7 (3)	C23—C24—C25—C26	−0.2 (7)
N3—Cu1—N4—C16	−6.0 (3)	C23—C24—C25—S1	179.6 (4)
N1—Cu1—N4—C16	84.9 (3)	O2—S1—C25—C26	124.7 (4)
O1—Cu1—N4—C16	−95.4 (3)	O3—S1—C25—C26	0.3 (4)
N2—Cu1—N4—C20	−2.0 (4)	O1—S1—C25—C26	−118.2 (4)
N3—Cu1—N4—C20	179.3 (4)	O2—S1—C25—C24	−55.1 (4)
N1—Cu1—N4—C20	−89.8 (4)	O3—S1—C25—C24	−179.5 (4)
O1—Cu1—N4—C20	89.9 (4)	O1—S1—C25—C24	62.0 (4)
C5—N1—C1—C2	1.8 (7)	C22—C21—C26—C25	0.9 (7)
Cu1—N1—C1—C2	−176.9 (4)	C27—C21—C26—C25	179.5 (4)
N1—C1—C2—C3	−0.1 (8)	C24—C25—C26—C21	−0.4 (7)
C1—C2—C3—C4	−0.7 (8)	S1—C25—C26—C21	179.8 (3)
C2—C3—C4—C5	−0.3 (7)	C26—C21—C27—O5	−174.9 (5)
C1—N1—C5—C4	−2.9 (6)	C22—C21—C27—O5	3.6 (7)
Cu1—N1—C5—C4	176.1 (3)	C26—C21—C27—O6	2.9 (7)
C1—N1—C5—C6	177.2 (4)	C22—C21—C27—O6	−178.6 (4)
Cu1—N1—C5—C6	−3.8 (5)	C33—C28—C29—O10	−179.8 (4)
C3—C4—C5—N1	2.2 (7)	C34—C28—C29—O10	−0.5 (7)
C3—C4—C5—C6	−177.9 (4)	C33—C28—C29—C30	−0.7 (6)
C10—N2—C6—C7	0.1 (7)	C34—C28—C29—C30	178.6 (4)
Cu1—N2—C6—C7	−175.1 (4)	O10—C29—C30—C31	178.4 (4)
C10—N2—C6—C5	180.0 (4)	C28—C29—C30—C31	−0.7 (7)
Cu1—N2—C6—C5	4.8 (5)	C29—C30—C31—C32	0.8 (7)
N1—C5—C6—N2	−0.4 (5)	C30—C31—C32—C33	0.5 (7)
C4—C5—C6—N2	179.6 (4)	C30—C31—C32—S2	−177.3 (4)
N1—C5—C6—C7	179.4 (4)	O9—S2—C32—C33	0.5 (4)
C4—C5—C6—C7	−0.5 (7)	O7—S2—C32—C33	122.3 (3)
N2—C6—C7—C8	−1.4 (7)	O8—S2—C32—C33	−120.0 (3)
C5—C6—C7—C8	178.7 (4)	O9—S2—C32—C31	178.3 (4)
C6—C7—C8—C9	1.1 (8)	O7—S2—C32—C31	−59.9 (4)
C7—C8—C9—C10	0.4 (8)	O8—S2—C32—C31	57.8 (4)
C6—N2—C10—C9	1.6 (7)	C31—C32—C33—C28	−1.9 (6)
Cu1—N2—C10—C9	176.3 (4)	S2—C32—C33—C28	176.0 (3)
C8—C9—C10—N2	−1.8 (8)	C29—C28—C33—C32	2.0 (6)
C15—N3—C11—C12	2.0 (7)	C34—C28—C33—C32	−177.3 (4)
Cu1—N3—C11—C12	−178.6 (4)	C29—C28—C34—O11	3.5 (7)
N3—C11—C12—C13	−0.1 (8)	C33—C28—C34—O11	−177.2 (4)
C11—C12—C13—C14	−1.5 (8)	C29—C28—C34—O12	−174.3 (4)
C12—C13—C14—C15	1.1 (8)	C33—C28—C34—O12	4.9 (6)
C11—N3—C15—C14	−2.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O5	0.85 (1)	1.82 (2)	2.625 (6)	158 (6)
O6—H6o···O7	0.85 (1)	1.78 (2)	2.609 (5)	164 (5)
O10—H10o···O11	0.85 (1)	1.87 (3)	2.634 (5)	149 (6)
O12—H12o···O8^i	0.85 (1)	1.77 (2)	2.589 (4)	163 (5)

Symmetry code: (i) x+1, y, z.