Aqua­[bis­(2-pyridylmeth­yl)amine][chelidonato(1.5–)]copper(II) chelidonate(0.5–) monohydrate

Fainerman-Melnikova, M.; Clegg, J.K.; Codd, R.

doi:10.1107/S1600536806050677

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Aqua[bis(2-pyridylmethyl)amine][chelidonato(1.5–)]copper(II) chelidonate(0.5–) monohydrate

M. Fainerman-Melnikova, J. K. Clegg and R. Codd

In the title compound, [Cu(C₇H_2.5O₆)(C₁₂H₁₃N₃)(H₂O)](C₇H_3.5O₆)·H₂O, chelidonic acid coordinates to a [Cu^II(dpa)(H₂O)]²⁺ core [dpa = bis(2-pyridylmethyl)amine] unit via a deprotonated carboxylic acid group. There is a three-dimensional hydrogen-bonding and π–π interaction network present in the structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050677/ng2166sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050677/ng2166Isup2.hkl Contains datablock I

CCDC reference: 630198

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.042
wR factor = 0.102
Data-to-parameter ratio = 14.5

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 ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.30
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C18    -   C19    ...       1.53 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1N    ..  O5      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  O7      ..       2.68 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C26 H23 Cu1 N3 O14
            Atom count from _chemical_formula_moiety:C33 H28.5 Cu1 N3 O192

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

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

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), WinGX32 (Farrugia, 1999), POV-RAY 3.5 (Cason, 2002) and WebLab ViewerPro 3.7 (Molecular Simulations, 2000); software used to prepare material for publication: enCIFer 1.0 (Allen et al., 2004).

Aqua[bis(2-pyridylmethyl)amine][chelidonato(1.5-)]copper(II) chelidonate(0.5-) monohydrate top

Crystal data top

[Cu(C₇H_2.5O₆)(C₁₂H₁₃N₃)(H₂O)](C₇H_3.5O₆)·H₂O	Z = 2
M_r = 665.03	F(000) = 682
Triclinic, P1	D_x = 1.721 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0667 (19) Å	Cell parameters from 3840 reflections
b = 12.705 (3) Å	θ = 1.7–27.6°
c = 13.688 (4) Å	µ = 0.94 mm⁻¹
α = 91.861 (6)°	T = 150 K
β = 107.121 (4)°	Needle, blue
γ = 105.337 (4)°	0.32 × 0.08 × 0.06 mm
V = 1283.7 (6) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	5981 independent reflections
Radiation source: sealed tube	4603 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −10→10
T_min = 0.794, T_max = 0.949	k = −16→16
12779 measured reflections	l = −18→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0463P)² + 0.5834P] where P = (F_o² + 2F_c²)/3
5981 reflections	(Δ/σ)_max = 0.001
412 parameters	Δρ_max = 0.47 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. 72 standard reflections were obtained by recollecting the first 50 CCD frames at the end of data collection. They were then used for a decay correction, giving an overall decay of 0.07%.

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5447 (3)	0.2006 (2)	0.50922 (19)	0.0180 (5)
H1	0.5034	0.2522	0.4670	0.022*
C2	0.6815 (3)	0.1633 (2)	0.49416 (19)	0.0192 (5)
H2	0.7345	0.1890	0.4428	0.023*
C3	0.7407 (3)	0.0875 (2)	0.55526 (19)	0.0193 (5)
H3	0.8337	0.0595	0.5456	0.023*
C4	0.6628 (3)	0.0530 (2)	0.6307 (2)	0.0194 (5)
H4	0.7025	0.0015	0.6738	0.023*
C5	0.5259 (3)	0.0945 (2)	0.64244 (19)	0.0174 (5)
C6A	0.4343 (4)	0.0628 (2)	0.7226 (2)	0.0197 (5)	0.67
H6A1	0.3347	−0.0063	0.6967	0.024*	0.67
H6A2	0.5222	0.0507	0.7859	0.024*	0.67
C7A	0.2051 (3)	0.1193 (2)	0.7866 (2)	0.0194 (5)	0.67
H7A1	0.2487	0.1144	0.8614	0.023*	0.67
H7A2	0.1229	0.0466	0.7518	0.023*	0.67
C6B	0.4343 (4)	0.0628 (2)	0.7226 (2)	0.0197 (5)	0.33
H6B1	0.4026	−0.0180	0.7227	0.024*	0.33
H6B2	0.5188	0.0970	0.7915	0.024*	0.33
C7B	0.2051 (3)	0.1193 (2)	0.7866 (2)	0.0194 (5)	0.33
H7B1	0.3094	0.1442	0.8504	0.023*	0.33
H7B2	0.1229	0.0504	0.7968	0.023*	0.33
C8	0.1062 (3)	0.2058 (2)	0.76646 (19)	0.0173 (5)
C9	−0.0017 (3)	0.2245 (2)	0.8231 (2)	0.0212 (6)
H9	−0.0153	0.1830	0.8782	0.025*
C10	−0.0895 (3)	0.3044 (2)	0.7986 (2)	0.0219 (6)
H10	−0.1651	0.3178	0.8363	0.026*
C11	−0.0670 (4)	0.3651 (2)	0.7187 (2)	0.0228 (6)
H11	−0.1249	0.4212	0.7015	0.027*
C12	0.0420 (3)	0.3418 (2)	0.6647 (2)	0.0194 (5)
H12	0.0579	0.3825	0.6095	0.023*
C13	0.0782 (3)	0.2005 (2)	0.40688 (18)	0.0147 (5)
C14	0.0552 (3)	0.2439 (2)	0.30295 (18)	0.0141 (5)
C15	0.1732 (3)	0.3345 (2)	0.28901 (19)	0.0168 (5)
H15	0.2702	0.3762	0.3465	0.020*
C16	0.1546 (3)	0.3690 (2)	0.18846 (19)	0.0173 (5)
C17	0.0037 (3)	0.2998 (2)	0.10768 (19)	0.0164 (5)
H17	−0.0160	0.3164	0.0387	0.020*
C18	−0.1104 (3)	0.2116 (2)	0.12833 (18)	0.0142 (5)
C19	−0.2764 (3)	0.1393 (2)	0.04377 (19)	0.0169 (5)
C20	0.2173 (3)	0.1075 (2)	0.11024 (19)	0.0170 (5)
C21	0.3849 (3)	0.2060 (2)	0.13646 (19)	0.0160 (5)
C22	0.4921 (3)	0.2418 (2)	0.2337 (2)	0.0191 (5)
H22	0.4654	0.2024	0.2876	0.023*
C23	0.6465 (4)	0.3380 (2)	0.2589 (2)	0.0212 (6)
C24	0.6688 (3)	0.3899 (2)	0.1681 (2)	0.0201 (5)
H24	0.7646	0.4553	0.1764	0.024*
C25	0.5578 (3)	0.3475 (2)	0.07400 (19)	0.0170 (5)
C26	0.5784 (3)	0.3919 (2)	−0.02366 (19)	0.0181 (5)
N1	0.4674 (3)	0.16671 (17)	0.58140 (15)	0.0160 (4)
N2B	0.2679 (10)	0.0985 (6)	0.7025 (5)	0.0179 (13)	0.33
H2N	0.191 (9)	0.042 (5)	0.657 (5)	0.027*	0.33
N2A	0.3626 (5)	0.1516 (3)	0.7454 (3)	0.0153 (6)	0.67
H1N	0.446 (4)	0.196 (3)	0.799 (2)	0.023*	0.67
N3	0.1260 (3)	0.26364 (17)	0.68764 (16)	0.0159 (4)
O1	0.1889 (2)	0.27185 (14)	0.48126 (13)	0.0186 (4)
O2	−0.0026 (2)	0.10494 (15)	0.41092 (14)	0.0229 (4)
O3	−0.0888 (2)	0.18184 (13)	0.22473 (12)	0.0139 (3)
O4	0.2647 (2)	0.45352 (15)	0.17445 (14)	0.0245 (4)
O5	−0.2984 (3)	0.16665 (17)	−0.04284 (14)	0.0287 (5)
O6	−0.3756 (2)	0.05972 (14)	0.07324 (13)	0.0185 (4)
H1B	−0.4590	0.0239	0.0214	0.028*	0.50
O7	0.1743 (2)	0.06776 (16)	0.18228 (14)	0.0245 (4)
O8	0.1361 (2)	0.07781 (15)	0.01409 (14)	0.0219 (4)
H1A	0.0489	0.0218	0.0059	0.033*	0.50
O9	0.4130 (2)	0.25632 (14)	0.05442 (13)	0.0170 (4)
O10	0.7512 (3)	0.37295 (17)	0.34723 (14)	0.0309 (5)
O11	0.4783 (3)	0.35085 (16)	−0.10817 (14)	0.0290 (5)
O12	0.7209 (3)	0.47828 (17)	−0.00313 (15)	0.0336 (5)
H2A	0.7322	0.4988	−0.0590	0.050*
O1W	0.4821 (3)	0.39883 (15)	0.65146 (14)	0.0261 (4)
H1W	0.5456	0.4142	0.6126	0.039*
H2W	0.5397	0.4293	0.7109	0.039*
O2W	0.3029 (4)	0.52869 (19)	0.48139 (18)	0.0478 (6)
H3W	0.2809	0.5667	0.5253	0.072*
H4W	0.2981	0.4664	0.5020	0.072*
Cu1	0.28929 (4)	0.22608 (3)	0.61927 (2)	0.01636 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0212 (13)	0.0176 (13)	0.0144 (12)	0.0040 (10)	0.0056 (10)	0.0030 (10)
C2	0.0204 (13)	0.0207 (14)	0.0145 (12)	0.0021 (11)	0.0059 (10)	0.0012 (10)
C3	0.0154 (12)	0.0204 (14)	0.0188 (13)	0.0018 (10)	0.0039 (10)	−0.0023 (11)
C4	0.0186 (13)	0.0177 (13)	0.0178 (13)	0.0043 (10)	0.0005 (10)	0.0017 (10)
C5	0.0174 (12)	0.0171 (13)	0.0138 (12)	0.0020 (10)	0.0019 (10)	0.0009 (10)
C6A	0.0229 (13)	0.0197 (13)	0.0176 (13)	0.0068 (11)	0.0068 (11)	0.0077 (10)
C7A	0.0237 (13)	0.0195 (13)	0.0175 (13)	0.0063 (11)	0.0098 (11)	0.0080 (10)
C6B	0.0229 (13)	0.0197 (13)	0.0176 (13)	0.0068 (11)	0.0068 (11)	0.0077 (10)
C7B	0.0237 (13)	0.0195 (13)	0.0175 (13)	0.0063 (11)	0.0098 (11)	0.0080 (10)
C8	0.0167 (12)	0.0159 (12)	0.0137 (12)	−0.0016 (10)	0.0021 (10)	0.0008 (10)
C9	0.0207 (13)	0.0248 (14)	0.0170 (13)	0.0024 (11)	0.0075 (11)	0.0051 (11)
C10	0.0191 (13)	0.0243 (14)	0.0220 (14)	0.0035 (11)	0.0089 (11)	0.0006 (11)
C11	0.0222 (13)	0.0202 (14)	0.0260 (14)	0.0088 (11)	0.0049 (11)	0.0020 (11)
C12	0.0207 (13)	0.0181 (13)	0.0189 (13)	0.0056 (10)	0.0050 (11)	0.0058 (10)
C13	0.0126 (11)	0.0181 (13)	0.0141 (12)	0.0047 (10)	0.0046 (10)	0.0033 (10)
C14	0.0148 (11)	0.0151 (12)	0.0125 (12)	0.0049 (10)	0.0044 (9)	−0.0004 (9)
C15	0.0170 (12)	0.0162 (12)	0.0121 (12)	−0.0008 (10)	0.0019 (10)	0.0008 (10)
C16	0.0179 (12)	0.0150 (12)	0.0176 (13)	0.0011 (10)	0.0065 (10)	0.0034 (10)
C17	0.0181 (12)	0.0199 (13)	0.0104 (11)	0.0047 (10)	0.0038 (10)	0.0049 (10)
C18	0.0153 (11)	0.0172 (12)	0.0095 (11)	0.0047 (10)	0.0030 (9)	0.0011 (9)
C19	0.0144 (12)	0.0182 (13)	0.0155 (12)	0.0019 (10)	0.0036 (10)	−0.0002 (10)
C20	0.0157 (12)	0.0173 (13)	0.0185 (13)	0.0045 (10)	0.0057 (10)	0.0057 (10)
C21	0.0179 (12)	0.0164 (12)	0.0169 (12)	0.0058 (10)	0.0089 (10)	0.0051 (10)
C22	0.0209 (13)	0.0207 (13)	0.0168 (13)	0.0044 (11)	0.0085 (11)	0.0059 (10)
C23	0.0215 (13)	0.0229 (14)	0.0187 (13)	0.0046 (11)	0.0071 (11)	0.0008 (11)
C24	0.0207 (13)	0.0164 (13)	0.0205 (13)	−0.0002 (10)	0.0077 (11)	0.0013 (10)
C25	0.0174 (12)	0.0137 (12)	0.0193 (13)	0.0015 (10)	0.0073 (10)	0.0027 (10)
C26	0.0211 (13)	0.0152 (13)	0.0171 (13)	0.0012 (10)	0.0078 (11)	0.0036 (10)
N1	0.0179 (10)	0.0159 (11)	0.0111 (10)	0.0025 (8)	0.0021 (8)	0.0017 (8)
N2B	0.018 (4)	0.023 (4)	0.013 (3)	0.004 (3)	0.007 (3)	0.003 (3)
N2A	0.0166 (17)	0.0124 (16)	0.0123 (16)	−0.0006 (14)	0.0024 (14)	−0.0006 (13)
N3	0.0146 (10)	0.0146 (10)	0.0151 (10)	0.0009 (8)	0.0024 (8)	0.0018 (8)
O1	0.0216 (9)	0.0188 (9)	0.0117 (9)	0.0035 (7)	0.0019 (7)	0.0029 (7)
O2	0.0274 (10)	0.0191 (10)	0.0181 (9)	−0.0010 (8)	0.0075 (8)	0.0050 (8)
O3	0.0123 (8)	0.0162 (9)	0.0104 (8)	0.0005 (7)	0.0026 (7)	0.0017 (7)
O4	0.0262 (10)	0.0204 (10)	0.0170 (9)	−0.0078 (8)	0.0052 (8)	0.0038 (8)
O5	0.0275 (10)	0.0329 (11)	0.0126 (9)	−0.0074 (9)	0.0009 (8)	0.0057 (8)
O6	0.0162 (9)	0.0185 (9)	0.0132 (9)	−0.0028 (7)	0.0004 (7)	0.0008 (7)
O7	0.0234 (10)	0.0280 (11)	0.0193 (10)	0.0010 (8)	0.0073 (8)	0.0114 (8)
O8	0.0225 (9)	0.0190 (9)	0.0188 (9)	−0.0041 (8)	0.0074 (8)	0.0034 (8)
O9	0.0169 (9)	0.0165 (9)	0.0139 (9)	−0.0012 (7)	0.0044 (7)	0.0044 (7)
O10	0.0347 (11)	0.0329 (12)	0.0147 (10)	−0.0019 (9)	0.0031 (9)	0.0013 (8)
O11	0.0312 (11)	0.0261 (11)	0.0173 (10)	−0.0073 (9)	0.0029 (9)	0.0045 (8)
O12	0.0352 (12)	0.0326 (12)	0.0162 (10)	−0.0162 (9)	0.0062 (9)	0.0046 (9)
O1W	0.0278 (10)	0.0245 (10)	0.0181 (10)	−0.0017 (8)	0.0047 (8)	−0.0042 (8)
O2W	0.0843 (19)	0.0359 (13)	0.0445 (14)	0.0268 (13)	0.0420 (14)	0.0176 (11)
Cu1	0.02003 (17)	0.01831 (17)	0.01273 (16)	0.00683 (13)	0.00650 (12)	0.00563 (12)

Geometric parameters (Å, º) top

C1—N1	1.341 (3)	C17—C18	1.345 (3)
C1—C2	1.375 (4)	C17—H17	0.9500
C1—H1	0.9500	C18—O3	1.359 (3)
C2—C3	1.383 (4)	C18—C19	1.531 (3)
C2—H2	0.9500	C19—O5	1.222 (3)
C3—C4	1.385 (4)	C19—O6	1.271 (3)
C3—H3	0.9500	C20—O7	1.220 (3)
C4—C5	1.390 (4)	C20—O8	1.278 (3)
C4—H4	0.9500	C20—C21	1.521 (3)
C5—N1	1.345 (3)	C21—C22	1.342 (4)
C5—C6A	1.504 (3)	C21—O9	1.357 (3)
C6A—N2A	1.461 (4)	C22—C23	1.442 (4)
C6A—H6A1	0.9900	C22—H22	0.9500
C6A—H6A2	0.9900	C23—O10	1.240 (3)
C7A—N2A	1.504 (4)	C23—C24	1.460 (4)
C7A—C8	1.508 (4)	C24—C25	1.332 (4)
C7A—H7A1	0.9900	C24—H24	0.9500
C7A—H7A2	0.9900	C25—O9	1.363 (3)
C8—N3	1.350 (3)	C25—C26	1.504 (3)
C8—C9	1.383 (4)	C26—O11	1.204 (3)
C9—C10	1.381 (4)	C26—O12	1.314 (3)
C9—H9	0.9500	N1—Cu1	1.972 (2)
C10—C11	1.386 (4)	N2B—Cu1	2.010 (7)
C10—H10	0.9500	N2B—H2N	0.890 (10)
C11—C12	1.384 (4)	N2A—Cu1	2.007 (3)
C11—H11	0.9500	N2A—H1N	0.886 (10)
C12—N3	1.339 (3)	N3—Cu1	1.967 (2)
C12—H12	0.9500	O1—Cu1	1.9956 (18)
C13—O2	1.229 (3)	O6—H1B	0.8365
C13—O1	1.277 (3)	O8—H1A	0.8354
C13—C14	1.520 (3)	O12—H2A	0.8388
C14—C15	1.345 (3)	O1W—Cu1	2.2713 (19)
C14—O3	1.359 (3)	O1W—H1W	0.8354
C15—C16	1.436 (3)	O1W—H2W	0.8306
C15—H15	0.9500	O2W—H3W	0.8455
C16—O4	1.260 (3)	O2W—H4W	0.8443
C16—C17	1.434 (3)

N1—C1—C2	122.4 (2)	O5—C19—C18	116.0 (2)
N1—C1—H1	118.8	O6—C19—C18	115.6 (2)
C2—C1—H1	118.8	O7—C20—O8	127.8 (2)
C1—C2—C3	118.8 (2)	O7—C20—C21	117.0 (2)
C1—C2—H2	120.6	O8—C20—C21	115.2 (2)
C3—C2—H2	120.6	C22—C21—O9	123.2 (2)
C2—C3—C4	119.2 (2)	C22—C21—C20	122.2 (2)
C2—C3—H3	120.4	O9—C21—C20	114.7 (2)
C4—C3—H3	120.4	C21—C22—C23	122.1 (2)
C3—C4—C5	119.2 (2)	C21—C22—H22	118.9
C3—C4—H4	120.4	C23—C22—H22	118.9
C5—C4—H4	120.4	O10—C23—C22	124.4 (2)
N1—C5—C4	121.1 (2)	O10—C23—C24	123.1 (2)
N1—C5—C6A	115.9 (2)	C22—C23—C24	112.5 (2)
C4—C5—C6A	123.1 (2)	C25—C24—C23	121.4 (2)
N2A—C6A—C5	108.4 (2)	C25—C24—H24	119.3
N2A—C6A—H6A1	110.0	C23—C24—H24	119.3
C5—C6A—H6A1	110.0	C24—C25—O9	123.7 (2)
N2A—C6A—H6A2	110.0	C24—C25—C26	124.6 (2)
C5—C6A—H6A2	110.0	O9—C25—C26	111.6 (2)
H6A1—C6A—H6A2	108.4	O11—C26—O12	125.9 (2)
N2A—C7A—C8	107.9 (2)	O11—C26—C25	123.5 (2)
N2A—C7A—H7A1	110.1	O12—C26—C25	110.6 (2)
C8—C7A—H7A1	110.1	C1—N1—C5	119.4 (2)
N2A—C7A—H7A2	110.1	C1—N1—Cu1	125.64 (17)
C8—C7A—H7A2	110.1	C5—N1—Cu1	114.59 (17)
H7A1—C7A—H7A2	108.5	Cu1—N2B—H2N	104 (6)
N3—C8—C9	121.1 (2)	C6A—N2A—C7A	115.9 (3)
N3—C8—C7A	116.0 (2)	C6A—N2A—Cu1	110.1 (2)
C9—C8—C7A	122.9 (2)	C7A—N2A—Cu1	108.2 (2)
C10—C9—C8	119.1 (2)	C6A—N2A—H1N	108 (3)
C10—C9—H9	120.5	C7A—N2A—H1N	101 (3)
C8—C9—H9	120.5	Cu1—N2A—H1N	114 (3)
C9—C10—C11	119.9 (2)	C12—N3—C8	119.6 (2)
C9—C10—H10	120.1	C12—N3—Cu1	125.86 (18)
C11—C10—H10	120.1	C8—N3—Cu1	114.50 (17)
C12—C11—C10	118.1 (2)	C13—O1—Cu1	120.33 (16)
C12—C11—H11	120.9	C14—O3—C18	118.11 (19)
C10—C11—H11	120.9	C19—O6—H1B	108.1
N3—C12—C11	122.2 (2)	C20—O8—H1A	109.5
N3—C12—H12	118.9	C21—O9—C25	117.09 (19)
C11—C12—H12	118.9	C26—O12—H2A	108.3
O2—C13—O1	127.9 (2)	Cu1—O1W—H1W	115.8
O2—C13—C14	119.4 (2)	Cu1—O1W—H2W	122.2
O1—C13—C14	112.6 (2)	H1W—O1W—H2W	110.6
C15—C14—O3	122.7 (2)	H3W—O2W—H4W	106.8
C15—C14—C13	122.3 (2)	N3—Cu1—N1	165.10 (8)
O3—C14—C13	115.0 (2)	N3—Cu1—O1	99.04 (8)
C14—C15—C16	120.9 (2)	N1—Cu1—O1	95.33 (8)
C14—C15—H15	119.6	N3—Cu1—N2A	82.88 (11)
C16—C15—H15	119.6	N1—Cu1—N2A	82.27 (11)
O4—C16—C17	123.9 (2)	O1—Cu1—N2A	169.27 (11)
O4—C16—C15	121.4 (2)	N3—Cu1—N2B	82.77 (19)
C17—C16—C15	114.7 (2)	N1—Cu1—N2B	83.36 (19)
C18—C17—C16	120.8 (2)	O1—Cu1—N2B	143.4 (2)
C18—C17—H17	119.6	N3—Cu1—O1W	94.53 (8)
C16—C17—H17	119.6	N1—Cu1—O1W	90.95 (8)
C17—C18—O3	122.8 (2)	O1—Cu1—O1W	83.52 (7)
C17—C18—C19	121.5 (2)	N2A—Cu1—O1W	106.92 (11)
O3—C18—C19	115.6 (2)	N2B—Cu1—O1W	133.0 (2)
O5—C19—O6	128.3 (2)

N1—C1—C2—C3	0.5 (4)	C8—C7A—N2A—C6A	−158.3 (2)
C1—C2—C3—C4	−1.1 (4)	C8—C7A—N2A—Cu1	−34.1 (3)
C2—C3—C4—C5	0.6 (4)	C11—C12—N3—C8	−0.6 (4)
C3—C4—C5—N1	0.5 (4)	C11—C12—N3—Cu1	−178.12 (19)
C3—C4—C5—C6A	−179.4 (2)	C9—C8—N3—C12	1.0 (4)
N1—C5—C6A—N2A	−25.0 (3)	C7A—C8—N3—C12	179.8 (2)
C4—C5—C6A—N2A	155.0 (3)	C9—C8—N3—Cu1	178.77 (19)
N2A—C7A—C8—N3	24.6 (3)	C7A—C8—N3—Cu1	−2.4 (3)
N2A—C7A—C8—C9	−156.6 (3)	O2—C13—O1—Cu1	13.0 (3)
N3—C8—C9—C10	−0.4 (4)	C14—C13—O1—Cu1	−164.90 (14)
C7A—C8—C9—C10	−179.1 (2)	C15—C14—O3—C18	1.8 (3)
C8—C9—C10—C11	−0.7 (4)	C13—C14—O3—C18	−175.54 (19)
C9—C10—C11—C12	1.0 (4)	C17—C18—O3—C14	−0.5 (3)
C10—C11—C12—N3	−0.4 (4)	C19—C18—O3—C14	−179.26 (19)
O2—C13—C14—C15	−161.3 (2)	C22—C21—O9—C25	−0.2 (3)
O1—C13—C14—C15	16.8 (3)	C20—C21—O9—C25	177.7 (2)
O2—C13—C14—O3	16.1 (3)	C24—C25—O9—C21	−1.3 (4)
O1—C13—C14—O3	−165.86 (19)	C26—C25—O9—C21	177.3 (2)
O3—C14—C15—C16	−1.5 (4)	C12—N3—Cu1—N1	167.8 (3)
C13—C14—C15—C16	175.6 (2)	C8—N3—Cu1—N1	−9.8 (4)
C14—C15—C16—O4	−179.8 (2)	C12—N3—Cu1—O1	−27.5 (2)
C14—C15—C16—C17	−0.1 (4)	C8—N3—Cu1—O1	154.88 (17)
O4—C16—C17—C18	−178.9 (2)	C12—N3—Cu1—N2A	163.1 (2)
C15—C16—C17—C18	1.4 (4)	C8—N3—Cu1—N2A	−14.46 (19)
C16—C17—C18—O3	−1.1 (4)	C12—N3—Cu1—N2B	−170.6 (3)
C16—C17—C18—C19	177.6 (2)	C8—N3—Cu1—N2B	11.8 (3)
C17—C18—C19—O5	0.0 (4)	C12—N3—Cu1—O1W	56.6 (2)
O3—C18—C19—O5	178.8 (2)	C8—N3—Cu1—O1W	−120.98 (17)
C17—C18—C19—O6	−178.7 (2)	C1—N1—Cu1—N3	−167.1 (3)
O3—C18—C19—O6	0.1 (3)	C5—N1—Cu1—N3	5.7 (4)
O7—C20—C21—C22	6.4 (4)	C1—N1—Cu1—O1	28.2 (2)
O8—C20—C21—C22	−174.9 (2)	C5—N1—Cu1—O1	−159.05 (17)
O7—C20—C21—O9	−171.5 (2)	C1—N1—Cu1—N2A	−162.4 (2)
O8—C20—C21—O9	7.2 (3)	C5—N1—Cu1—N2A	10.42 (19)
O9—C21—C22—C23	0.5 (4)	C1—N1—Cu1—N2B	171.4 (3)
C20—C21—C22—C23	−177.2 (2)	C5—N1—Cu1—N2B	−15.8 (3)
C21—C22—C23—O10	−178.6 (3)	C1—N1—Cu1—O1W	−55.4 (2)
C21—C22—C23—C24	0.4 (4)	C5—N1—Cu1—O1W	117.37 (18)
O10—C23—C24—C25	177.3 (3)	C13—O1—Cu1—N3	−98.52 (18)
C22—C23—C24—C25	−1.8 (4)	C13—O1—Cu1—N1	77.55 (18)
C23—C24—C25—O9	2.3 (4)	C13—O1—Cu1—N2A	1.0 (6)
C23—C24—C25—C26	−176.1 (2)	C13—O1—Cu1—N2B	−8.5 (4)
C24—C25—C26—O11	178.5 (3)	C13—O1—Cu1—O1W	167.90 (18)
O9—C25—C26—O11	−0.1 (4)	C6A—N2A—Cu1—N3	154.7 (2)
C24—C25—C26—O12	−0.1 (4)	C7A—N2A—Cu1—N3	27.2 (2)
O9—C25—C26—O12	−178.7 (2)	C6A—N2A—Cu1—N1	−24.0 (2)
C2—C1—N1—C5	0.7 (4)	C7A—N2A—Cu1—N1	−151.6 (2)
C2—C1—N1—Cu1	173.14 (19)	C6A—N2A—Cu1—O1	53.7 (7)
C4—C5—N1—C1	−1.2 (4)	C7A—N2A—Cu1—O1	−73.9 (6)
C6A—C5—N1—C1	178.8 (2)	C6A—N2A—Cu1—N2B	66.7 (5)
C4—C5—N1—Cu1	−174.43 (19)	C7A—N2A—Cu1—N2B	−60.9 (5)
C6A—C5—N1—Cu1	5.5 (3)	C6A—N2A—Cu1—O1W	−112.7 (2)
C5—C6A—N2A—C7A	155.1 (2)	C7A—N2A—Cu1—O1W	119.7 (2)
C5—C6A—N2A—Cu1	31.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1N···O11ⁱ	0.89 (1)	2.22 (3)	2.935 (4)	137 (4)
N2A—H1N···O5ⁱⁱ	0.89 (1)	2.63 (3)	3.307 (4)	134 (3)
O8—H1A···O8ⁱⁱⁱ	0.84	1.63	2.457 (3)	173
O8—H1A···O7ⁱⁱⁱ	0.84	2.68	3.191 (3)	121
O12—H2A···O4^iv	0.84	1.71	2.550 (3)	174
O1W—H1W···O2W^v	0.84	2.05	2.878 (3)	173
O1W—H2W···O4^v	0.83	2.08	2.861 (3)	157
O2W—H3W···O10^v	0.85	2.00	2.821 (3)	165
O2W—H4W···O1	0.84	2.37	3.147 (3)	153
O2W—H4W···O1W	0.84	2.47	3.124 (3)	134
N2B—H2N···O2^vi	0.89 (1)	2.05 (3)	2.920 (8)	164 (8)
O6—H1B···O6^vii	0.84	1.65	2.485 (3)	173

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

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