Bis(2,2′-bipyridine-κN,N′){[5-(carboxy­methyl­sulfanyl)-1,3,4-thia­diazol-2-ylsulfanyl]acetato-κO}copper(II) [5-(carboxy­methyl­sulfan­yl)-1,3,4-thia­diazol-2-ylsulfan­yl]acetate dihydrate

Gao, S.; Huo, L.-H.; Zhao, H.; Ng, S.W.

doi:10.1107/S1600536804032647

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Bis(2,2′-bipyridine-κN,N′){[5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2-ylsulfanyl]acetato-κO}copper(II) [5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2-ylsulfanyl]acetate dihydrate

S. Gao, L.-H. Huo, H. Zhao and S. W. Ng

In the title compound, [Cu(C₆H₅N₂O₄S₃)(C₁₀H₈N₂)₂](C₆H₅N₂O₄S₃)·2H₂O, the Cu^II atom is coordinated by four N atoms from two bipyridine ligands and one O atom from the [5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2-ylsulfanyl]acetate unit. The five-coordinate environment is intermediate between a trigonal bipyramid and a square pyramid. The complex cations and anions are connected with the water molecules via O—H

O hydrogen bonds to form layers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032647/ob6456sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032647/ob6456Isup2.hkl Contains datablock I

CCDC reference: 262264

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.052
wR factor = 0.156
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C32
PLAT731_ALERT_1_B Bond    Calc     0.85(5), Rep   0.860(10) ......       5.00 su-Rat
              O2W  -H2W2    1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(5), Rep   0.860(10) ......       5.00 su-Rat
              O2W  -H4#     1.555   1.555

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.605     0.856
            Tmin' and Tmax expected:      0.700     0.852
            RR' =      0.860
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S2     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S5     in Main Residue .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H1W2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.860(10) ......       4.00 su-Rat
              O2W  -H2W1    1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      109(5), Rep      109(2) ......       2.50 su-Rat
              H2W1 -O2W  -H2W2    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(4), Rep   0.850(10) ......       4.00 su-Rat
              O1W  -H1#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.860(10) ......       4.00 su-Rat
              O2W  -H3#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.84(5), Rep     1.84(2) ......       2.50 su-Rat
              H4#  -O1W     1.555   1.555

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

  12 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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-κN,N'){[5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2- ylsulfanyl]acetato-κO}copper(II) 5-(carboxymethylsulfanyl)-1,3,4-thiadiazol-2-ylsulfanylacetate dihydrate top

Crystal data top

[Cu(C₆H₅N₂O₄S₃)(C₁₀H₈N₂)₂](C₆H₅N₂O₄S₃)·2H₂O	Z = 2
M_r = 942.54	F(000) = 966
Triclinic, P1	D_x = 1.597 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.900 (2) Å	Cell parameters from 16305 reflections
b = 12.197 (2) Å	θ = 3.2–27.5°
c = 14.772 (3) Å	µ = 0.94 mm⁻¹
α = 91.86 (1)°	T = 295 K
β = 91.53 (2)°	Block, blue
γ = 92.28 (1)°	0.37 × 0.26 × 0.17 mm
V = 1960.6 (7) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	8693 independent reflections
Radiation source: fine-focus sealed tube	6237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scan	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→14
T_min = 0.605, T_max = 0.856	k = −15→15
18913 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.091P)² + 0.5195P] where P = (F_o² + 2F_c²)/3
8693 reflections	(Δ/σ)_max = 0.001
541 parameters	Δρ_max = 0.69 e Å⁻³
14 restraints	Δρ_min = −0.44 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.49685 (3)	0.49718 (3)	0.26028 (2)	0.0375 (1)
S1	0.0565 (1)	0.4230 (1)	0.3333 (1)	0.0556 (3)
S2	−0.0963 (1)	0.6143 (1)	0.2847 (1)	0.0542 (2)
S3	−0.1645 (1)	0.7719 (1)	0.1407 (1)	0.0638 (3)
S4	0.0929 (1)	−0.1312 (1)	0.3123 (1)	0.0742 (3)
S5	0.0698 (1)	−0.2121 (1)	0.5035 (1)	0.0615 (3)
S6	0.1311 (1)	−0.1629 (1)	0.7018 (1)	0.0638 (3)
O1	0.3231 (2)	0.4618 (2)	0.2928 (2)	0.045 (1)
O2	0.3285 (3)	0.3436 (2)	0.1757 (2)	0.059 (1)
O3	0.0513 (4)	0.8840 (3)	0.0594 (3)	0.090 (1)
O4	0.0171 (5)	0.8331 (4)	−0.0835 (3)	0.114 (2)
O5	0.3140 (4)	0.1269 (4)	0.3158 (3)	0.074 (1)	0.735 (6)
O6	0.3619 (4)	−0.0468 (4)	0.2879 (4)	0.077 (2)	0.735 (6)
O5'	0.379 (1)	0.062 (1)	0.294 (1)	0.074 (1)	0.265 (6)
O6'	0.358 (1)	−0.119 (1)	0.313 (1)	0.077 (2)	0.265 (6)
O7	0.4011 (3)	−0.0214 (5)	0.7084 (3)	0.110 (2)
O8	0.3764 (4)	−0.0677 (5)	0.8472 (3)	0.127 (2)
O1w	0.3840 (4)	0.1235 (4)	0.1080 (2)	0.085 (1)
O2w	0.2475 (3)	−0.0125 (4)	−0.0029 (3)	0.093 (1)
N1	0.4509 (2)	0.6010 (2)	0.1668 (2)	0.042 (1)
N2	0.6282 (2)	0.4644 (2)	0.1680 (2)	0.040 (1)
N3	0.5886 (2)	0.6203 (2)	0.3489 (2)	0.037 (1)
N4	0.5589 (2)	0.4049 (2)	0.3593 (2)	0.039 (1)
N5	0.0616 (3)	0.5353 (3)	0.1776 (2)	0.051 (1)
N6	0.0083 (3)	0.6193 (3)	0.1321 (2)	0.053 (1)
N7	0.1622 (4)	−0.0242 (3)	0.4689 (2)	0.068 (1)
N8	0.1719 (3)	−0.0311 (3)	0.5606 (2)	0.065 (1)
C1	0.3589 (3)	0.6702 (3)	0.1737 (3)	0.052 (1)
C2	0.3424 (4)	0.7516 (4)	0.1126 (3)	0.067 (1)
C3	0.4204 (4)	0.7602 (4)	0.0412 (3)	0.071 (1)
C4	0.5140 (4)	0.6874 (4)	0.0330 (3)	0.059 (1)
C5	0.5273 (3)	0.6092 (3)	0.0968 (2)	0.040 (1)
C6	0.6252 (3)	0.5288 (3)	0.0954 (2)	0.040 (1)
C7	0.7086 (3)	0.5181 (3)	0.0268 (2)	0.053 (1)
C8	0.7974 (4)	0.4412 (4)	0.0351 (3)	0.065 (1)
C9	0.8013 (4)	0.3775 (4)	0.1084 (3)	0.062 (1)
C10	0.7147 (3)	0.3902 (3)	0.1735 (3)	0.054 (1)
C11	0.6043 (3)	0.7274 (3)	0.3376 (2)	0.047 (1)
C12	0.6689 (4)	0.7973 (3)	0.3994 (3)	0.056 (1)
C13	0.7193 (4)	0.7531 (4)	0.4754 (3)	0.060 (1)
C14	0.7031 (3)	0.6426 (3)	0.4878 (2)	0.051 (1)
C15	0.6387 (3)	0.5772 (3)	0.4236 (2)	0.038 (1)
C16	0.6185 (3)	0.4573 (3)	0.4303 (2)	0.038 (1)
C17	0.6543 (3)	0.3993 (3)	0.5058 (2)	0.050 (1)
C18	0.6304 (4)	0.2878 (4)	0.5069 (3)	0.057 (1)
C19	0.5730 (4)	0.2352 (3)	0.4345 (3)	0.060 (1)
C20	0.5375 (3)	0.2961 (3)	0.3608 (3)	0.052 (1)
C21	0.2764 (3)	0.3865 (3)	0.2407 (2)	0.042 (1)
C22	0.1502 (3)	0.3394 (3)	0.2619 (3)	0.051 (1)
C23	0.0166 (3)	0.5229 (3)	0.2579 (2)	0.046 (1)
C24	−0.0744 (3)	0.6675 (3)	0.1779 (2)	0.048 (1)
C25	−0.1228 (4)	0.7735 (4)	0.0238 (3)	0.070 (1)
C26	−0.0095 (5)	0.8339 (4)	−0.0065 (4)	0.075 (1)
C27	0.2863 (5)	0.0303 (4)	0.2961 (4)	0.060 (2)	0.735 (6)
C28	0.1531 (6)	−0.0030 (6)	0.2749 (7)	0.061 (2)	0.735 (6)
C27'	0.317 (2)	−0.026 (1)	0.302 (2)	0.060 (2)	0.265 (6)
C28'	0.181 (2)	−0.009 (2)	0.291 (3)	0.061 (2)	0.265 (6)
C29	0.1120 (4)	−0.1115 (3)	0.4291 (3)	0.057 (1)
C30	0.1304 (3)	−0.1234 (3)	0.5893 (3)	0.052 (1)
C31	0.1983 (4)	−0.0411 (4)	0.7600 (3)	0.062 (1)
C32	0.3376 (4)	−0.0433 (4)	0.7732 (3)	0.062 (1)
H3o	0.1112	0.9212	0.0387	0.107*
H7o	0.4763	−0.0168	0.7254	0.132*
H1w1	0.450 (3)	0.095 (4)	0.126 (3)	0.102*
H1w2	0.357 (4)	0.164 (4)	0.150 (2)	0.102*
H2w1	0.272 (5)	−0.029 (5)	−0.056 (2)	0.111*
H2w2	0.302 (4)	0.029 (4)	0.025 (3)	0.111*
H1	0.3048	0.6630	0.2210	0.062*
H2	0.2794	0.8002	0.1195	0.081*
H3	0.4103	0.8142	−0.0010	0.085*
H4	0.5671	0.6914	−0.0152	0.071*
H7	0.7048	0.5617	−0.0236	0.063*
H8	0.8548	0.4331	−0.0099	0.078*
H9	0.8614	0.3260	0.1146	0.074*
H10	0.7164	0.3454	0.2233	0.065*
H11	0.5704	0.7569	0.2859	0.056*
H12	0.6778	0.8721	0.3896	0.067*
H13	0.7638	0.7975	0.5180	0.072*
H14	0.7355	0.6117	0.5395	0.061*
H17	0.6940	0.4359	0.5552	0.060*
H18	0.6536	0.2486	0.5571	0.068*
H19	0.5574	0.1597	0.4341	0.071*
H20	0.4977	0.2601	0.3112	0.062*
H22a	0.1603	0.2699	0.2907	0.061*
H22b	0.1054	0.3239	0.2050	0.061*
H25a	−0.1169	0.6976	0.0034	0.084*
H25b	−0.1916	0.8023	−0.0095	0.084*
H28a	0.1409	−0.0029	0.2097	0.074*	0.735 (6)
H28b	0.1033	0.0540	0.3003	0.074*	0.735 (6)
H28c	0.1625	0.0136	0.2297	0.074*	0.265 (6)
H28d	0.1581	0.0494	0.3325	0.074*	0.265 (6)
H31a	0.1784	0.0226	0.7257	0.074*
H31b	0.1616	−0.0331	0.8188	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0341 (2)	0.0451 (2)	0.0334 (2)	0.0016 (2)	0.0003 (2)	0.0052 (2)
S1	0.0427 (5)	0.0736 (7)	0.0511 (5)	−0.0029 (4)	0.0053 (4)	0.0165 (4)
S2	0.0465 (5)	0.0635 (6)	0.0528 (5)	0.0018 (4)	0.0139 (4)	−0.0034 (4)
S3	0.0590 (6)	0.0574 (6)	0.0755 (7)	0.0155 (5)	−0.0013 (5)	−0.0055 (5)
S4	0.0825 (8)	0.0728 (8)	0.0637 (6)	−0.0280 (6)	−0.0098 (6)	−0.0066 (5)
S5	0.0574 (6)	0.0520 (6)	0.0734 (6)	−0.0129 (4)	−0.0058 (5)	−0.0001 (5)
S6	0.0657 (6)	0.0587 (6)	0.0663 (6)	−0.0082 (5)	−0.0068 (5)	0.0111 (5)
O1	0.036 (1)	0.057 (2)	0.040 (1)	−0.005 (1)	0.001 (1)	0.002 (1)
O2	0.059 (2)	0.064 (2)	0.054 (2)	−0.003 (1)	0.010 (1)	−0.005 (1)
O3	0.080 (2)	0.083 (3)	0.105 (3)	0.000 (2)	−0.012 (2)	0.018 (2)
O4	0.139 (4)	0.106 (3)	0.097 (3)	−0.008 (3)	0.039 (3)	−0.009 (2)
O5	0.077 (3)	0.051 (3)	0.094 (3)	−0.008 (2)	0.000 (2)	0.002 (2)
O6	0.074 (3)	0.053 (3)	0.105 (4)	0.009 (2)	0.006 (3)	−0.003 (2)
O5'	0.077 (3)	0.051 (3)	0.094 (3)	−0.008 (2)	0.000 (2)	0.002 (2)
O6'	0.074 (3)	0.053 (3)	0.105 (4)	0.009 (2)	0.006 (3)	−0.003 (2)
O7	0.057 (2)	0.175 (5)	0.101 (3)	0.014 (2)	0.000 (2)	0.026 (3)
O8	0.069 (2)	0.224 (6)	0.090 (3)	0.013 (3)	−0.018 (2)	0.046 (3)
O1w	0.081 (2)	0.098 (3)	0.076 (2)	0.005 (2)	−0.013 (2)	−0.002 (2)
O2w	0.073 (2)	0.089 (3)	0.114 (3)	−0.008 (2)	−0.008 (2)	−0.008 (2)
N1	0.040 (1)	0.045 (2)	0.040 (1)	0.001 (1)	−0.004 (1)	0.003 (1)
N2	0.037 (1)	0.047 (2)	0.036 (1)	0.002 (1)	0.002 (1)	0.000 (1)
N3	0.036 (1)	0.044 (2)	0.031 (1)	0.001 (1)	0.001 (1)	0.003 (1)
N4	0.035 (1)	0.044 (2)	0.039 (1)	−0.001 (1)	0.004 (1)	0.006 (1)
N5	0.040 (2)	0.066 (2)	0.049 (2)	0.012 (1)	0.006 (1)	0.009 (1)
N6	0.046 (2)	0.067 (2)	0.046 (2)	0.011 (1)	0.005 (1)	0.004 (1)
N7	0.082 (2)	0.060 (2)	0.060 (2)	−0.024 (2)	−0.004 (2)	−0.007 (2)
N8	0.071 (2)	0.055 (2)	0.067 (2)	−0.018 (2)	−0.002 (2)	0.004 (2)
C1	0.047 (2)	0.056 (2)	0.053 (2)	0.014 (2)	−0.003 (2)	0.005 (2)
C2	0.066 (3)	0.059 (3)	0.078 (3)	0.018 (2)	−0.013 (2)	0.007 (2)
C3	0.074 (3)	0.069 (3)	0.073 (3)	0.009 (2)	−0.002 (2)	0.034 (2)
C4	0.058 (2)	0.064 (3)	0.057 (2)	−0.004 (2)	0.001 (2)	0.019 (2)
C5	0.039 (2)	0.049 (2)	0.032 (1)	−0.008 (1)	−0.006 (1)	0.002 (1)
C6	0.040 (2)	0.048 (2)	0.030 (1)	−0.006 (1)	−0.003 (1)	−0.003 (1)
C7	0.052 (2)	0.068 (3)	0.037 (2)	−0.013 (2)	0.007 (2)	−0.002 (2)
C8	0.050 (2)	0.089 (3)	0.055 (2)	−0.001 (2)	0.020 (2)	−0.019 (2)
C9	0.047 (2)	0.079 (3)	0.060 (2)	0.015 (2)	0.007 (2)	−0.011 (2)
C10	0.052 (2)	0.062 (2)	0.048 (2)	0.015 (2)	0.002 (2)	−0.002 (2)
C11	0.049 (2)	0.049 (2)	0.043 (2)	−0.008 (2)	0.000 (2)	0.003 (1)
C12	0.062 (2)	0.047 (2)	0.056 (2)	−0.012 (2)	0.005 (2)	−0.002 (2)
C13	0.054 (2)	0.071 (3)	0.052 (2)	−0.015 (2)	−0.003 (2)	−0.014 (2)
C14	0.047 (2)	0.067 (3)	0.038 (2)	−0.000 (2)	−0.007 (2)	−0.001 (2)
C15	0.030 (1)	0.053 (2)	0.031 (1)	0.002 (1)	0.005 (1)	0.002 (1)
C16	0.028 (1)	0.053 (2)	0.033 (1)	0.007 (1)	0.007 (1)	0.005 (1)
C17	0.047 (2)	0.065 (2)	0.040 (2)	0.015 (2)	0.004 (2)	0.010 (2)
C18	0.056 (2)	0.067 (3)	0.051 (2)	0.021 (2)	0.010 (2)	0.022 (2)
C19	0.058 (2)	0.047 (2)	0.075 (3)	0.009 (2)	0.014 (2)	0.018 (2)
C20	0.052 (2)	0.047 (2)	0.057 (2)	0.002 (2)	0.000 (2)	0.007 (2)
C21	0.039 (2)	0.049 (2)	0.038 (2)	0.002 (1)	−0.003 (1)	0.012 (1)
C22	0.044 (2)	0.052 (2)	0.056 (2)	−0.005 (2)	−0.003 (2)	0.007 (2)
C23	0.032 (2)	0.057 (2)	0.048 (2)	−0.002 (1)	0.002 (2)	0.001 (2)
C24	0.042 (2)	0.053 (2)	0.049 (2)	−0.001 (2)	0.001 (2)	−0.003 (2)
C25	0.073 (3)	0.065 (3)	0.073 (3)	0.007 (2)	−0.014 (2)	0.014 (2)
C26	0.085 (3)	0.050 (3)	0.090 (3)	0.015 (2)	−0.020 (3)	−0.004 (2)
C27	0.064 (4)	0.058 (4)	0.058 (3)	−0.001 (3)	−0.001 (3)	0.009 (3)
C28	0.066 (4)	0.069 (3)	0.048 (5)	−0.005 (3)	−0.017 (3)	0.007 (2)
C27'	0.064 (4)	0.058 (4)	0.058 (3)	−0.001 (3)	−0.001 (3)	0.009 (3)
C28'	0.066 (4)	0.069 (3)	0.048 (5)	−0.005 (3)	−0.017 (3)	0.007 (2)
C29	0.052 (2)	0.053 (2)	0.065 (2)	−0.006 (2)	−0.002 (2)	−0.001 (2)
C30	0.043 (2)	0.053 (2)	0.059 (2)	−0.001 (2)	−0.004 (2)	−0.001 (2)
C31	0.061 (2)	0.062 (3)	0.061 (2)	0.008 (2)	−0.002 (2)	−0.006 (2)
C32	0.058 (2)	0.064 (3)	0.064 (2)	0.001 (2)	−0.004 (2)	0.003 (2)

Geometric parameters (Å, º) top

Cu1—O1	2.001 (2)	C8—C9	1.354 (6)
Cu1—N1	1.972 (3)	C9—C10	1.375 (5)
Cu1—N2	2.045 (3)	C11—C12	1.387 (5)
Cu1—N3	2.157 (3)	C12—C13	1.373 (6)
Cu1—N4	1.994 (3)	C13—C14	1.371 (6)
S1—C23	1.737 (4)	C14—C15	1.378 (5)
S1—C22	1.807 (4)	C15—C16	1.478 (5)
S2—C23	1.738 (3)	C16—C17	1.395 (4)
S2—C24	1.744 (4)	C17—C18	1.376 (6)
S3—C24	1.733 (4)	C18—C19	1.353 (6)
S3—C25	1.797 (5)	C19—C20	1.393 (5)
S4—C29	1.740 (4)	C21—C22	1.514 (5)
S4—C28	1.782 (5)	C25—C26	1.499 (7)
S4—C28'	1.783 (9)	C27—C28	1.514 (8)
S5—C29	1.731 (4)	C27'—C28'	1.52 (1)
S5—C30	1.739 (4)	C31—C32	1.528 (6)
S6—C30	1.746 (4)	O3—H3o	0.85
S6—C31	1.811 (5)	O7—H7o	0.85
O1—C21	1.262 (4)	O1w—H1w1	0.85 (1)
O2—C21	1.239 (4)	O1w—H1w2	0.85 (1)
O3—C26	1.286 (6)	O2w—H2w1	0.86 (1)
O4—C26	1.181 (6)	O2w—H2w2	0.86 (1)
O5—C27	1.228 (5)	C1—H1	0.93
O6—C27	1.280 (5)	C2—H2	0.93
O5'—C27'	1.256 (8)	C3—H3	0.93
O6'—C27'	1.242 (9)	C4—H4	0.93
O7—C32	1.227 (5)	C7—H7	0.93
O8—C32	1.211 (6)	C8—H8	0.93
N1—C1	1.341 (4)	C9—H9	0.93
N1—C5	1.348 (4)	C10—H10	0.93
N2—C10	1.335 (4)	C11—H11	0.93
N2—C6	1.350 (4)	C12—H12	0.93
N3—C11	1.327 (4)	C13—H13	0.93
N3—C15	1.349 (4)	C14—H14	0.93
N4—C20	1.340 (5)	C17—H17	0.93
N4—C16	1.348 (4)	C18—H18	0.93
N5—C23	1.307 (4)	C19—H19	0.93
N5—N6	1.382 (4)	C20—H20	0.93
N6—C24	1.291 (4)	C22—H22a	0.97
N7—C29	1.295 (5)	C22—H22b	0.97
N7—N8	1.360 (5)	C25—H25a	0.97
N8—C30	1.285 (5)	C25—H25b	0.97
C1—C2	1.378 (6)	C28—H28a	0.97
C2—C3	1.376 (6)	C28—H28b	0.97
C3—C4	1.384 (6)	C28'—H28c	0.97
C4—C5	1.371 (5)	C28'—H28d	0.97
C5—C6	1.478 (5)	C31—H31a	0.97
C6—C7	1.386 (5)	C31—H31b	0.97
C7—C8	1.380 (6)

O1—Cu1—N1	94.0 (1)	O6—C27—C28	115.3 (6)
O1—Cu1—N2	143.8 (1)	C27—C28—S4	119.3 (4)
O1—Cu1—N3	113.7 (1)	O6'—C27'—O5'	127 (2)
O1—Cu1—N4	90.9 (1)	O6'—C27'—C28'	122 (1)
N1—Cu1—N2	80.7 (1)	O5'—C27'—C28'	111 (1)
N1—Cu1—N3	94.9 (1)	C27'—C28'—S4	111 (1)
N1—Cu1—N4	173.3 (1)	N7—C29—S5	113.4 (3)
N2—Cu1—N3	102.4 (1)	N7—C29—S4	124.6 (3)
N2—Cu1—N4	97.9 (1)	S5—C29—S4	122.0 (2)
N3—Cu1—N4	79.0 (1)	N8—C30—S5	113.5 (3)
C23—S1—C22	100.2 (2)	N8—C30—S6	126.1 (3)
C23—S2—C24	86.6 (2)	S5—C30—S6	120.3 (2)
C24—S3—C25	100.0 (2)	C32—C31—S6	113.5 (3)
C29—S4—C28	100.6 (4)	O8—C32—O7	125.2 (5)
C29—S4—C28'	93 (1)	O8—C32—C31	116.9 (4)
C29—S5—C30	86.6 (2)	O7—C32—C31	117.8 (4)
C30—S6—C31	101.5 (2)	C26—O3—H3o	109.5
C21—O1—Cu1	110.5 (2)	C32—O7—H7o	109.5
C1—N1—C5	119.2 (3)	H1w1—O1w—H1w2	110 (2)
C1—N1—Cu1	124.4 (2)	H2w1—O2w—H2w2	109 (2)
C5—N1—Cu1	116.0 (2)	N1—C1—H1	119.2
C10—N2—C6	118.7 (3)	C2—C1—H1	119.2
C10—N2—Cu1	127.4 (2)	C3—C2—H2	120.5
C6—N2—Cu1	113.8 (2)	C1—C2—H2	120.5
C11—N3—C15	118.5 (3)	C2—C3—H3	120.4
C11—N3—Cu1	129.1 (2)	C4—C3—H3	120.4
C15—N3—Cu1	112.4 (2)	C5—C4—H4	120.5
C20—N4—C16	119.3 (3)	C3—C4—H4	120.5
C20—N4—Cu1	123.3 (2)	C8—C7—H7	120.8
C16—N4—Cu1	117.3 (2)	C6—C7—H7	120.8
C23—N5—N6	112.3 (3)	C9—C8—H8	119.9
C24—N6—N5	113.3 (3)	C7—C8—H8	119.9
C29—N7—N8	113.3 (4)	C8—C9—H9	120.6
C30—N8—N7	113.2 (3)	C10—C9—H9	120.6
N1—C1—C2	121.7 (4)	N2—C10—H10	118.7
C3—C2—C1	119.1 (4)	C9—C10—H10	118.7
C2—C3—C4	119.3 (4)	N3—C11—H11	118.4
C5—C4—C3	119.0 (4)	C12—C11—H11	118.4
N1—C5—C4	121.7 (3)	C13—C12—H12	120.9
N1—C5—C6	114.8 (3)	C11—C12—H12	120.9
C4—C5—C6	123.5 (3)	C14—C13—H13	120.4
N2—C6—C7	121.3 (3)	C12—C13—H13	120.4
N2—C6—C5	114.3 (3)	C13—C14—H14	120.0
C7—C6—C5	124.4 (3)	C15—C14—H14	120.0
C8—C7—C6	118.4 (4)	C18—C17—H17	120.2
C9—C8—C7	120.2 (4)	C16—C17—H17	120.2
C8—C9—C10	118.8 (4)	C19—C18—H18	120.1
N2—C10—C9	122.5 (4)	C17—C18—H18	120.1
N3—C11—C12	123.1 (3)	C18—C19—H19	120.5
C13—C12—C11	118.1 (4)	C20—C19—H19	120.5
C14—C13—C12	119.1 (4)	N4—C20—H20	119.1
C13—C14—C15	120.0 (3)	C19—C20—H20	119.1
N3—C15—C14	121.2 (3)	C21—C22—H22a	108.1
N3—C15—C16	115.1 (3)	S1—C22—H22a	108.1
C14—C15—C16	123.8 (3)	C21—C22—H22b	108.1
N4—C16—C17	120.4 (3)	S1—C22—H22b	108.1
N4—C16—C15	116.1 (3)	H22a—C22—H22b	107.3
C17—C16—C15	123.5 (3)	C26—C25—H25a	106.8
C18—C17—C16	119.6 (4)	S3—C25—H25a	106.8
C19—C18—C17	119.8 (3)	C26—C25—H25b	106.8
C18—C19—C20	119.0 (4)	S3—C25—H25b	106.8
N4—C20—C19	121.9 (4)	H25a—C25—H25b	106.6
O2—C21—O1	125.0 (3)	C27—C28—H28a	107.5
O2—C21—C22	116.9 (3)	S4—C28—H28a	107.5
O1—C21—C22	117.9 (3)	C27—C28—H28b	107.5
C21—C22—S1	116.9 (3)	S4—C28—H28b	107.5
N5—C23—S1	125.7 (3)	H28a—C28—H28b	107.0
N5—C23—S2	113.9 (3)	C27'—C28'—H28c	109.4
S1—C23—S2	120.3 (2)	S4—C28'—H28c	109.4
N6—C24—S3	126.1 (3)	C27'—C28'—H28d	109.4
N6—C24—S2	113.8 (3)	S4—C28'—H28d	109.4
S3—C24—S2	120.0 (2)	H28c—C28'—H28d	108.0
C26—C25—S3	122.3 (4)	C32—C31—H31a	108.9
O4—C26—O3	126.0 (6)	S6—C31—H31a	108.9
O4—C26—C25	121.3 (5)	C32—C31—H31b	108.9
O3—C26—C25	112.7 (5)	S6—C31—H31b	108.9
O5—C27—O6	125.6 (6)	H31a—C31—H31b	107.7
O5—C27—C28	119.1 (6)

N1—Cu1—O1—C21	85.4 (2)	C11—N3—C15—C14	1.1 (4)
N4—Cu1—O1—C21	−99.1 (2)	Cu1—N3—C15—C14	179.0 (2)
N2—Cu1—O1—C21	5.7 (3)	C11—N3—C15—C16	−179.2 (3)
N3—Cu1—O1—C21	−177.4 (2)	Cu1—N3—C15—C16	−1.3 (3)
O1—Cu1—N1—C1	37.7 (3)	C13—C14—C15—N3	−1.4 (5)
N2—Cu1—N1—C1	−178.4 (3)	C13—C14—C15—C16	178.9 (3)
N3—Cu1—N1—C1	−76.5 (3)	C20—N4—C16—C17	−1.9 (4)
O1—Cu1—N1—C5	−149.8 (2)	Cu1—N4—C16—C17	174.0 (2)
N2—Cu1—N1—C5	−5.9 (2)	C20—N4—C16—C15	180.0 (3)
N3—Cu1—N1—C5	96.0 (2)	Cu1—N4—C16—C15	−4.2 (3)
N1—Cu1—N2—C10	−178.2 (3)	N3—C15—C16—N4	3.5 (4)
N4—Cu1—N2—C10	8.4 (3)	C14—C15—C16—N4	−176.7 (3)
O1—Cu1—N2—C10	−94.2 (3)	N3—C15—C16—C17	−174.5 (3)
N3—Cu1—N2—C10	88.8 (3)	C14—C15—C16—C17	5.2 (5)
N1—Cu1—N2—C6	3.3 (2)	N4—C16—C17—C18	1.2 (5)
N4—Cu1—N2—C6	−170.1 (2)	C15—C16—C17—C18	179.2 (3)
O1—Cu1—N2—C6	87.4 (3)	C16—C17—C18—C19	0.3 (5)
N3—Cu1—N2—C6	−89.6 (2)	C17—C18—C19—C20	−1.0 (6)
N1—Cu1—N3—C11	−0.3 (3)	C16—N4—C20—C19	1.2 (5)
N4—Cu1—N3—C11	177.0 (3)	Cu1—N4—C20—C19	−174.4 (3)
O1—Cu1—N3—C11	−96.9 (3)	C18—C19—C20—N4	0.2 (6)
N2—Cu1—N3—C11	81.2 (3)	Cu1—O1—C21—O2	−3.1 (4)
N1—Cu1—N3—C15	−177.9 (2)	Cu1—O1—C21—C22	172.9 (2)
N4—Cu1—N3—C15	−0.62 (19)	O2—C21—C22—S1	−163.0 (3)
O1—Cu1—N3—C15	85.5 (2)	O1—C21—C22—S1	20.7 (4)
N2—Cu1—N3—C15	−96.4 (2)	C23—S1—C22—C21	73.0 (3)
O1—Cu1—N4—C20	64.3 (3)	N6—N5—C23—S1	177.6 (3)
N2—Cu1—N4—C20	−80.4 (3)	N6—N5—C23—S2	0.1 (4)
N3—Cu1—N4—C20	178.3 (3)	C22—S1—C23—N5	−8.3 (4)
O1—Cu1—N4—C16	−111.3 (2)	C22—S1—C23—S2	169.0 (2)
N2—Cu1—N4—C16	103.9 (2)	C24—S2—C23—N5	0.0 (3)
N3—Cu1—N4—C16	2.6 (2)	C24—S2—C23—S1	−177.6 (2)
C23—N5—N6—C24	−0.2 (5)	N5—N6—C24—S3	−177.1 (3)
C29—N7—N8—C30	0.7 (6)	N5—N6—C24—S2	0.2 (4)
C5—N1—C1—C2	−1.9 (6)	C25—S3—C24—N6	7.6 (4)
Cu1—N1—C1—C2	170.3 (3)	C25—S3—C24—S2	−169.5 (2)
N1—C1—C2—C3	1.8 (7)	C23—S2—C24—N6	−0.1 (3)
C1—C2—C3—C4	−0.5 (7)	C23—S2—C24—S3	177.4 (2)
C2—C3—C4—C5	−0.6 (7)	C24—S3—C25—C26	−83.0 (4)
C1—N1—C5—C4	0.7 (5)	S3—C25—C26—O4	179.2 (4)
Cu1—N1—C5—C4	−172.2 (3)	S3—C25—C26—O3	−0.9 (6)
C1—N1—C5—C6	−179.8 (3)	O5—C27—C28—S4	−142.0 (7)
Cu1—N1—C5—C6	7.3 (4)	O6—C27—C28—S4	40.7 (10)
C3—C4—C5—N1	0.6 (6)	C29—S4—C28—C27	61.8 (8)
C3—C4—C5—C6	−178.9 (4)	O6'—C27'—C28'—S4	8 (4)
C10—N2—C6—C7	0.8 (5)	O5'—C27'—C28'—S4	−174 (2)
Cu1—N2—C6—C7	179.5 (3)	C29—S4—C28'—C27'	78 (2)
C10—N2—C6—C5	−179.1 (3)	N8—N7—C29—S5	0.6 (5)
Cu1—N2—C6—C5	−0.5 (3)	N8—N7—C29—S4	−176.9 (3)
N1—C5—C6—N2	−4.3 (4)	C30—S5—C29—N7	−1.2 (3)
C4—C5—C6—N2	175.1 (3)	C30—S5—C29—S4	176.3 (3)
N1—C5—C6—C7	175.7 (3)	C28—S4—C29—N7	−2.2 (5)
C4—C5—C6—C7	−4.8 (5)	C28'—S4—C29—N7	7.4 (8)
N2—C6—C7—C8	−1.4 (5)	C28—S4—C29—S5	−179.4 (4)
C5—C6—C7—C8	178.5 (3)	C28'—S4—C29—S5	−169.8 (7)
C6—C7—C8—C9	0.6 (6)	N7—N8—C30—S5	−1.7 (5)
C7—C8—C9—C10	0.7 (7)	N7—N8—C30—S6	178.3 (3)
C6—N2—C10—C9	0.5 (6)	C29—S5—C30—N8	1.6 (3)
Cu1—N2—C10—C9	−177.9 (3)	C29—S5—C30—S6	−178.3 (3)
C8—C9—C10—N2	−1.3 (7)	C31—S6—C30—N8	1.7 (4)
C15—N3—C11—C12	−0.6 (5)	C31—S6—C30—S5	−178.3 (2)
Cu1—N3—C11—C12	−178.1 (3)	C30—S6—C31—C32	−92.5 (3)
N3—C11—C12—C13	0.3 (6)	S6—C31—C32—O8	−100.3 (5)
C11—C12—C13—C14	−0.6 (6)	S6—C31—C32—O7	79.1 (5)
C12—C13—C14—C15	1.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w2···O2	0.85 (1)	2.24 (4)	2.926 (5)	137 (5)
O1w—H1w1···O8ⁱ	0.85 (1)	1.97 (2)	2.793 (5)	163 (6)
O2w—H2w1···O8ⁱⁱ	0.86 (1)	1.91 (2)	2.733 (6)	161 (5)
O2w—H2w2···O1w	0.86 (1)	1.84 (2)	2.673 (5)	163 (5)
O3—H3o···O2wⁱⁱⁱ	0.85	1.80	2.643 (5)	174
O7—H7o···O5′ⁱ	0.85	1.72	2.47 (1)	146
O7—H7o···O6ⁱ	0.85	1.92	2.680 (6)	149

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

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