μ-4,4′-Bipyridine-κ²N:N′-bis­{[N-(2-amino­ethyl)-1,3-propyl­diamine-κ³N,N′,N′′]aqua­copper(II)} tetra­kis(perchlorate)

The title dinuclear copper complex, [{Cu(C₅H₁₅N₃)(H₂O)}₂(C₁₀H₈N₂)](ClO₄)₄, has a crystallographically imposed inversion centre. Each Cu^II atom is coordinated by four N atoms [Cu—N = 2.001 (4)–2.037 (4) Å] and one water mol­ecule [Cu—O = 2.373 (3) Å] in a slightly distorted square-pyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in solvent or counterion
• R factor = 0.061
• wR factor = 0.160
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cu1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.64
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      41.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C6     -   C7     ...       1.43 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N4  -CU1 -N2  -C6     97.10  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            N2  -CU1 -N4  -C10   -50.80  1.80   1.555   1.555   1.555   1.555
PLAT731_ALERT_1_C Bond    Calc    1.407(5), Rep    1.408(2) ......       2.50 su-Ra
              CL1  -O2      1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.10 Deg.
              O4   -CL1  -O4'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      18.10 Deg.
              O5   -CL1  -O5'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.50 Deg.
              O3   -CL1  -O3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      29.30 Deg.
              O9   -CL2  -O8'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.60 Deg.
              O7   -CL2  -O7'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      38.10 Deg.
              O8   -CL2  -O9'     1.555   1.555   1.555

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:   C20 H42 Cl4 Cu2 N8 O18
            Atom count from _chemical_formula_moiety:C20 H42 Cl8 Cu2 N8 O34
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  24 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
  14 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXLTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

µ₂-4,4'-Bipyridine-κ²N:N'-bis{[N-(2-aminoethyl)-1,3-propyldiamine- κ³N,N',N'']aquacopper(II)} tetrakis(perchlorate)

Crystal data

[Cu2(C10H21N4O)2](ClO4)4	F(000) = 976
Mr = 951.50	Dx = 1.677 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.6572 (9) Å	Cell parameters from 4327 reflections
b = 17.218 (2) Å	θ = 2.5–26.5°
c = 14.4430 (17) Å	µ = 1.49 mm^−1
β = 98.359 (2)°	T = 293 K
V = 1884.0 (4) Å^3	Block, blue
Z = 2	0.34 × 0.30 × 0.28 mm

Data collection

Bruker APEX area-dectector diffractometer	3311 independent reflections
Radiation source: fine-focus sealed tube	2755 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.631, Tmax = 0.680	k = −20→20
13315 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 2.7723P] where P = (Fo^2 + 2Fc^2)/3
3311 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.78 e Å^−3
511 restraints	Δρmin = −0.42 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	0.30576 (8)	0.22001 (3)	0.63203 (4)	0.0494 (2)
Cl1	0.0696 (3)	0.01588 (11)	0.24452 (14)	0.0989 (7)
Cl2	0.6592 (2)	0.22192 (10)	0.46318 (12)	0.0824 (5)
N1	0.1955 (5)	0.3237 (2)	0.5875 (3)	0.0541 (10)
N2	0.1856 (6)	0.1678 (3)	0.5159 (3)	0.0640 (11)
H2A	0.0834	0.1928	0.4972	0.077*
H2B	0.2538	0.1741	0.4707	0.077*
N3	0.4579 (7)	0.1251 (3)	0.6707 (3)	0.0675 (12)
H3	0.5493	0.1282	0.6370	0.081*
N4	0.4523 (7)	0.2702 (3)	0.7417 (4)	0.0713 (13)
H4A	0.4937	0.3160	0.7242	0.086*
H4B	0.3851	0.2794	0.7868	0.086*
O1	0.0783 (6)	0.1877 (2)	0.7206 (3)	0.0807 (12)
H1A	0.0068	0.1499	0.7095	0.097*
H1B	0.0566	0.2087	0.7709	0.097*
O2	−0.0813 (6)	0.0533 (3)	0.2680 (5)	0.131 (2)
O3	0.065 (2)	−0.0117 (11)	0.1524 (5)	0.147 (5)	0.512 (19)
O4	0.2019 (13)	0.0733 (6)	0.2578 (13)	0.142 (5)	0.512 (19)
O5	0.117 (2)	−0.0444 (7)	0.3091 (10)	0.091 (4)	0.512 (19)
O6	0.7222 (13)	0.1532 (4)	0.5093 (7)	0.142 (4)	0.672 (8)
O7	0.8059 (8)	0.2521 (6)	0.4267 (6)	0.113 (3)	0.672 (8)
O8	0.5042 (9)	0.2162 (8)	0.3979 (6)	0.151 (4)	0.672 (8)
O9	0.6205 (13)	0.2669 (5)	0.5390 (5)	0.115 (3)	0.672 (8)
O3'	−0.006 (2)	−0.0410 (7)	0.1806 (10)	0.152 (5)	0.488 (19)
O4'	0.166 (2)	0.0647 (8)	0.1917 (13)	0.141 (5)	0.488 (19)
O5'	0.161 (2)	−0.0279 (10)	0.3189 (10)	0.115 (6)	0.488 (19)
O6'	0.617 (3)	0.2933 (6)	0.4173 (12)	0.147 (6)	0.328 (8)
O7'	0.8233 (14)	0.1980 (13)	0.4395 (14)	0.139 (6)	0.328 (8)
O8'	0.653 (3)	0.2312 (12)	0.5597 (4)	0.130 (6)	0.328 (8)
O9'	0.534 (2)	0.1675 (9)	0.4212 (13)	0.140 (6)	0.328 (8)
C1	0.0385 (9)	0.3450 (4)	0.6039 (6)	0.096 (2)
H1	−0.0220	0.3124	0.6397	0.115*
C2	−0.0413 (8)	0.4132 (4)	0.5708 (6)	0.094 (2)
H2	−0.1533	0.4252	0.5842	0.113*
C3	0.0415 (6)	0.4632 (2)	0.5187 (3)	0.0475 (11)
C4	0.2060 (7)	0.4412 (3)	0.5031 (4)	0.0603 (13)
H4	0.2706	0.4733	0.4690	0.072*
C5	0.2764 (7)	0.3721 (3)	0.5375 (4)	0.0645 (14)
H5	0.3880	0.3585	0.5247	0.077*
C6	0.1461 (8)	0.0842 (3)	0.5222 (5)	0.0743 (17)
H6A	0.0613	0.0770	0.5652	0.089*
H6B	0.0927	0.0657	0.4612	0.089*
C7	0.3007 (9)	0.0389 (4)	0.5535 (6)	0.090 (2)
H7A	0.3882	0.0503	0.5131	0.108*
H7B	0.2696	−0.0156	0.5450	0.108*
C8	0.3832 (10)	0.0498 (4)	0.6505 (6)	0.096 (2)
H8A	0.2954	0.0403	0.6913	0.115*
H8B	0.4755	0.0112	0.6650	0.115*
C9	0.5388 (10)	0.1376 (5)	0.7696 (4)	0.090 (2)
H9A	0.6374	0.1024	0.7860	0.108*
H9B	0.4526	0.1279	0.8113	0.108*
C10	0.6008 (9)	0.2197 (5)	0.7787 (5)	0.094 (2)
H10A	0.6409	0.2320	0.8439	0.112*
H10B	0.6983	0.2275	0.7437	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0570 (4)	0.0385 (3)	0.0513 (4)	0.0110 (2)	0.0031 (3)	0.0007 (2)
Cl1	0.1237 (15)	0.0794 (11)	0.1077 (14)	0.0317 (11)	0.0651 (12)	0.0278 (10)
Cl2	0.0796 (10)	0.0876 (11)	0.0888 (11)	0.0113 (8)	0.0421 (9)	0.0185 (9)
N1	0.052 (2)	0.038 (2)	0.073 (3)	0.0109 (18)	0.013 (2)	0.0041 (19)
N2	0.068 (3)	0.067 (3)	0.055 (2)	0.006 (2)	0.003 (2)	−0.006 (2)
N3	0.084 (3)	0.061 (3)	0.059 (3)	0.023 (2)	0.014 (2)	0.001 (2)
N4	0.078 (3)	0.063 (3)	0.072 (3)	−0.001 (2)	0.006 (2)	−0.010 (2)
O1	0.093 (3)	0.074 (3)	0.081 (3)	−0.010 (2)	0.033 (2)	0.003 (2)
O2	0.132 (4)	0.100 (4)	0.180 (6)	0.035 (3)	0.089 (4)	0.029 (4)
O3	0.176 (11)	0.195 (12)	0.086 (7)	0.067 (9)	0.068 (7)	0.027 (8)
O4	0.144 (9)	0.117 (8)	0.182 (11)	−0.004 (7)	0.087 (8)	0.068 (8)
O5	0.116 (8)	0.063 (6)	0.099 (8)	−0.011 (6)	0.032 (6)	0.018 (6)
O6	0.166 (8)	0.107 (6)	0.166 (8)	0.051 (6)	0.064 (6)	0.048 (6)
O7	0.103 (6)	0.144 (7)	0.104 (5)	0.008 (5)	0.053 (5)	0.032 (5)
O8	0.099 (6)	0.228 (11)	0.122 (7)	0.006 (7)	0.000 (5)	0.038 (7)
O9	0.113 (6)	0.141 (7)	0.103 (6)	0.058 (5)	0.054 (5)	0.020 (5)
O3'	0.199 (12)	0.142 (10)	0.124 (10)	0.000 (9)	0.051 (9)	0.038 (9)
O4'	0.174 (10)	0.145 (10)	0.125 (10)	0.011 (8)	0.097 (8)	0.056 (8)
O5'	0.141 (11)	0.109 (10)	0.100 (9)	0.029 (9)	0.039 (8)	0.019 (8)
O6'	0.177 (13)	0.142 (12)	0.123 (11)	0.037 (11)	0.029 (11)	0.015 (10)
O7'	0.119 (11)	0.167 (13)	0.137 (12)	0.056 (10)	0.039 (9)	0.011 (12)
O8'	0.146 (12)	0.159 (13)	0.094 (10)	0.015 (11)	0.044 (9)	0.054 (10)
O9'	0.137 (11)	0.148 (12)	0.135 (11)	0.013 (11)	0.025 (10)	0.033 (11)
C1	0.081 (4)	0.057 (3)	0.163 (6)	0.016 (3)	0.060 (4)	0.045 (4)
C2	0.068 (4)	0.061 (3)	0.167 (6)	0.025 (3)	0.062 (4)	0.043 (4)
C3	0.052 (3)	0.036 (2)	0.057 (3)	0.007 (2)	0.013 (2)	0.001 (2)
C4	0.052 (3)	0.058 (3)	0.074 (3)	0.011 (2)	0.021 (3)	0.023 (3)
C5	0.049 (3)	0.065 (3)	0.083 (4)	0.020 (2)	0.018 (3)	0.018 (3)
C6	0.063 (3)	0.069 (4)	0.089 (4)	−0.008 (3)	0.005 (3)	−0.027 (3)
C7	0.083 (4)	0.061 (4)	0.129 (6)	0.001 (3)	0.020 (4)	−0.025 (4)
C8	0.077 (4)	0.055 (4)	0.155 (7)	0.010 (3)	0.017 (5)	0.013 (4)
C9	0.094 (5)	0.109 (6)	0.066 (4)	0.049 (4)	0.005 (3)	0.017 (4)
C10	0.062 (4)	0.140 (7)	0.073 (4)	0.016 (4)	−0.012 (3)	−0.035 (4)

Geometric parameters (Å, º)

Cu1—N4	2.000 (5)	N4—C10	1.468 (8)
Cu1—N2	2.006 (4)	N4—H4A	0.9000
Cu1—N3	2.037 (4)	N4—H4B	0.9000
Cu1—N1	2.038 (4)	O1—H1A	0.8500
Cu1—O1	2.372 (4)	O1—H1B	0.8500
Cl1—O2	1.408 (2)	C1—C2	1.377 (8)
Cl1—O3	1.408 (3)	C1—H1	0.9300
Cl1—O5	1.408 (3)	C2—C3	1.359 (7)
Cl1—O4	1.408 (3)	C2—H2	0.9300
Cl1—O4'	1.411 (4)	C3—C4	1.365 (6)
Cl1—O5'	1.411 (4)	C3—C3^i	1.484 (8)
Cl1—O3'	1.412 (4)	C4—C5	1.369 (7)
Cl2—O8	1.408 (3)	C4—H4	0.9300
Cl2—O7	1.408 (3)	C5—H5	0.9300
Cl2—O9	1.408 (2)	C6—C7	1.436 (9)
Cl2—O6	1.408 (2)	C6—H6A	0.9700
Cl2—O8'	1.411 (4)	C6—H6B	0.9700
Cl2—O7'	1.411 (4)	C7—C8	1.462 (11)
Cl2—O9'	1.411 (4)	C7—H7A	0.9700
Cl2—O6'	1.412 (4)	C7—H7B	0.9700
N1—C1	1.311 (7)	C8—H8A	0.9700
N1—C5	1.315 (6)	C8—H8B	0.9700
N2—C6	1.475 (7)	C9—C10	1.491 (10)
N2—H2A	0.9000	C9—H9A	0.9700
N2—H2B	0.9000	C9—H9B	0.9700
N3—C8	1.431 (8)	C10—H10A	0.9700
N3—C9	1.488 (8)	C10—H10B	0.9700
N3—H3	0.9100
N4—Cu1—N2	173.2 (2)	Cu1—N2—H2A	108.0
N4—Cu1—N3	84.06 (19)	C6—N2—H2B	108.0
N2—Cu1—N3	92.54 (19)	Cu1—N2—H2B	108.0
N4—Cu1—N1	91.76 (18)	H2A—N2—H2B	107.2
N2—Cu1—N1	90.58 (18)	C8—N3—C9	115.2 (6)
N3—Cu1—N1	169.45 (19)	C8—N3—Cu1	118.4 (4)
N4—Cu1—O1	92.60 (19)	C9—N3—Cu1	106.8 (3)
N2—Cu1—O1	93.58 (18)	C8—N3—H3	105.1
N3—Cu1—O1	95.69 (18)	C9—N3—H3	105.1
N1—Cu1—O1	94.17 (16)	Cu1—N3—H3	105.1
O2—Cl1—O3	118.2 (6)	C10—N4—Cu1	110.4 (4)
O2—Cl1—O5	108.7 (8)	C10—N4—H4A	109.6
O3—Cl1—O5	110.2 (9)	Cu1—N4—H4A	109.6
O2—Cl1—O4	104.2 (6)	C10—N4—H4B	109.6
O3—Cl1—O4	106.5 (8)	Cu1—N4—H4B	109.6
O5—Cl1—O4	108.4 (8)	H4A—N4—H4B	108.1
O2—Cl1—O4'	111.6 (6)	Cu1—O1—H1A	125.5
O3—Cl1—O4'	68.6 (8)	Cu1—O1—H1B	127.7
O5—Cl1—O4'	133.7 (10)	H1A—O1—H1B	106.7
O4—Cl1—O4'	40.1 (7)	N1—C1—C2	123.2 (5)
O2—Cl1—O5'	113.2 (9)	N1—C1—H1	118.4
O3—Cl1—O5'	118.7 (11)	C2—C1—H1	118.4
O5—Cl1—O5'	18.1 (11)	C3—C2—C1	120.9 (5)
O4—Cl1—O5'	90.3 (9)	C3—C2—H2	119.5
O4'—Cl1—O5'	119.4 (9)	C1—C2—H2	119.5
O2—Cl1—O3'	101.6 (8)	C2—C3—C4	115.5 (4)
O3—Cl1—O3'	36.5 (6)	C2—C3—C3^i	122.3 (5)
O5—Cl1—O3'	87.9 (9)	C4—C3—C3^i	122.2 (5)
O4—Cl1—O3'	142.7 (8)	C3—C4—C5	120.4 (5)
O4'—Cl1—O3'	104.9 (8)	C3—C4—H4	119.8
O5'—Cl1—O3'	103.7 (9)	C5—C4—H4	119.8
O8—Cl2—O7	114.6 (6)	N1—C5—C4	123.9 (5)
O8—Cl2—O9	107.9 (6)	N1—C5—H5	118.1
O7—Cl2—O9	111.0 (6)	C4—C5—H5	118.1
O8—Cl2—O6	117.1 (7)	C7—C6—N2	112.5 (5)
O7—Cl2—O6	104.5 (5)	C7—C6—H6A	109.1
O9—Cl2—O6	101.0 (5)	N2—C6—H6A	109.1
O8—Cl2—O8'	121.6 (11)	C7—C6—H6B	109.1
O7—Cl2—O8'	118.1 (10)	N2—C6—H6B	109.1
O9—Cl2—O8'	29.3 (8)	H6A—C6—H6B	107.8
O6—Cl2—O8'	71.7 (9)	C6—C7—C8	117.0 (6)
O8—Cl2—O7'	120.7 (10)	C6—C7—H7A	108.1
O7—Cl2—O7'	39.6 (9)	C8—C7—H7A	108.1
O9—Cl2—O7'	130.2 (10)	C6—C7—H7B	108.1
O6—Cl2—O7'	67.3 (9)	C8—C7—H7B	108.1
O8'—Cl2—O7'	115.5 (11)	H7A—C7—H7B	107.3
O8—Cl2—O9'	38.1 (8)	N3—C8—C7	114.6 (6)
O7—Cl2—O9'	127.8 (10)	N3—C8—H8A	108.6
O9—Cl2—O9'	119.5 (10)	C7—C8—H8A	108.6
O6—Cl2—O9'	79.0 (9)	N3—C8—H8B	108.6
O8'—Cl2—O9'	112.4 (11)	C7—C8—H8B	108.6
O7'—Cl2—O9'	106.0 (10)	H8A—C8—H8B	107.6
O8—Cl2—O6'	68.5 (9)	N3—C9—C10	107.7 (5)
O7—Cl2—O6'	69.0 (9)	N3—C9—H9A	110.2
O9—Cl2—O6'	80.0 (8)	C10—C9—H9A	110.2
O6—Cl2—O6'	173.2 (10)	N3—C9—H9B	110.2
O8'—Cl2—O6'	109.1 (10)	C10—C9—H9B	110.2
O7'—Cl2—O6'	106.9 (10)	H9A—C9—H9B	108.5
O9'—Cl2—O6'	106.4 (10)	N4—C10—C9	108.0 (5)
C1—N1—C5	116.1 (4)	N4—C10—H10A	110.1
C1—N1—Cu1	122.5 (4)	C9—C10—H10A	110.1
C5—N1—Cu1	121.4 (3)	N4—C10—H10B	110.1
C6—N2—Cu1	117.3 (4)	C9—C10—H10B	110.1
C6—N2—H2A	108.0	H10A—C10—H10B	108.4
N4—Cu1—N1—C1	−99.8 (6)	N1—Cu1—N4—C10	−160.9 (5)
N2—Cu1—N1—C1	86.6 (6)	O1—Cu1—N4—C10	104.8 (5)
N3—Cu1—N1—C1	−166.2 (9)	C5—N1—C1—C2	0.7 (11)
O1—Cu1—N1—C1	−7.0 (6)	Cu1—N1—C1—C2	−177.0 (6)
N4—Cu1—N1—C5	82.6 (5)	N1—C1—C2—C3	−0.5 (13)
N2—Cu1—N1—C5	−91.0 (5)	C1—C2—C3—C4	−0.5 (11)
N3—Cu1—N1—C5	16.2 (12)	C1—C2—C3—C3^i	179.4 (7)
O1—Cu1—N1—C5	175.4 (4)	C2—C3—C4—C5	1.2 (9)
N4—Cu1—N2—C6	97.1 (16)	C3^i—C3—C4—C5	−178.8 (6)
N3—Cu1—N2—C6	37.4 (4)	C1—N1—C5—C4	0.0 (9)
N1—Cu1—N2—C6	−152.7 (4)	Cu1—N1—C5—C4	177.7 (5)
O1—Cu1—N2—C6	−58.4 (4)	C3—C4—C5—N1	−1.0 (9)
N4—Cu1—N3—C8	150.9 (5)	Cu1—N2—C6—C7	−56.6 (7)
N2—Cu1—N3—C8	−35.0 (5)	N2—C6—C7—C8	68.4 (8)
N1—Cu1—N3—C8	−142.1 (9)	C9—N3—C8—C7	178.7 (6)
O1—Cu1—N3—C8	58.8 (5)	Cu1—N3—C8—C7	50.6 (7)
N4—Cu1—N3—C9	18.9 (4)	C6—C7—C8—N3	−65.9 (9)
N2—Cu1—N3—C9	−167.0 (4)	C8—N3—C9—C10	−177.1 (5)
N1—Cu1—N3—C9	86.0 (10)	Cu1—N3—C9—C10	−43.4 (6)
O1—Cu1—N3—C9	−73.1 (4)	Cu1—N4—C10—C9	−35.9 (7)
N2—Cu1—N4—C10	−50.8 (18)	N3—C9—C10—N4	52.6 (7)
N3—Cu1—N4—C10	9.4 (5)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O7′^ii	0.90	2.05	2.880 (14)	154
N2—H2A···O7^ii	0.90	2.44	3.336 (10)	172
N2—H2B···O9′	0.90	2.36	3.17 (2)	150
N2—H2B···O8	0.90	2.43	3.280 (12)	158
N3—H3···O8′	0.91	2.30	2.972 (19)	131
N3—H3···O6	0.91	2.46	3.337 (10)	162
N4—H4A···O2^iii	0.90	2.43	3.078 (7)	129
N4—H4A···O4^iii	0.90	2.49	3.292 (14)	149
N4—H4A···O4′^iii	0.90	2.52	3.408 (16)	169
N4—H4B···O7^iv	0.90	2.26	3.067 (9)	149
N4—H4B···O7′^iv	0.90	2.35	3.202 (18)	157
O1—H1A···O5^v	0.85	2.05	2.886 (16)	168
O1—H1A···O3′^v	0.85	2.46	2.991 (17)	122
O1—H1A···O5′^v	0.85	2.46	3.31 (2)	171
O1—H1B···O6′^iv	0.85	2.10	2.832 (17)	144
O1—H1B···O8^iv	0.85	2.33	3.169 (13)	172

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