trans-{1,8-Bis[(S)-1-phenyl-eth-yl]-1,3,6,8,10,13-hexa-aza-cyclo-tetra-deca-ne}bis(thio-cyanato--κN)copper(II).

In the title thio-cyanate-coordinated aza-macrocyclic copper(II) complex, [Cu(NCS)(2)(C(24)H(38)N(6))], the Cu(II) atom is coordinated by the four secondary N atoms of the aza-macrocyclic ligand and by the two N atoms of the thio-cyanate ions in a tetra-gonally distorted octa-hedral geometry. The average equatorial Cu-N bond length is shorter than the average axial Cu-N bond length [2.010 (2) and 2.528 (4) Å, respectively]. An N-H⋯N hydrogen-bonding inter-action between the secondary amine N atom and the adjacent thio-cyanate ion leads to a polymeric chain along the a axis.

Related literature

For the potential applications of chiral metal complexes in chiral recognition and chiral catalysis, see: Katsuki et al. (2000 ▶); Lehn (1995 ▶) and as chiral building blocks, see: Du et al. (2003 ▶); Gao et al. (2005 ▶). It has been reported that the enanti­omers of [Ru(1,10-phenanthroline)3]2+ induce chiral aggregation of various achiral anionic porphyrins, see: Randazzo et al. (2008 ▶). For typical C—S bond lengths, see: Banerjee & Zubieta (2004 ▶); Stølevik & Postmyr (1997 ▶). For the preparation, see: Han et al. (2008 ▶).

Experimental

Crystal data

[Cu(NCS)2(C24H38N6)]

M = 590.30

Monoclinic,

a = 6.5976 (5) Å

b = 14.7609 (11) Å

c = 15.2847 (12) Å

β = 99.952 (2)°

V = 1466.13 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.92 mm−1

T = 195 K

0.38 × 0.26 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.751, T max = 0.871

10954 measured reflections

6272 independent reflections

4364 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.115

S = 1.11

6272 reflections

336 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.68 e Å−3

Absolute structure: Flack (1983 ▶), 2485 Friedel pairs

Flack parameter: −0.01 (2)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810026632/jh2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026632/jh2175Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(NCS)2(C24H38N6)]	F(000) = 622
Mr = 590.30	Dx = 1.337 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4491 reflections
a = 6.5976 (5) Å	θ = 2.7–27.9°
b = 14.7609 (11) Å	µ = 0.92 mm−1
c = 15.2847 (12) Å	T = 195 K
β = 99.952 (2)°	Block, purple
V = 1466.13 (19) Å3	0.38 × 0.26 × 0.15 mm
Z = 2

Siemens SMART CCD diffractometer	6272 independent reflections
Radiation source: fine-focus sealed tube	4364 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
Tmin = 0.751, Tmax = 0.871	k = −19→19
10954 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0195P)2 + 1.3207P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
6272 reflections	Δρmax = 0.69 e Å−3
336 parameters	Δρmin = −0.67 e Å−3
1 restraint	Absolute structure: Flack (1983), 2485 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (2)

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.

	x	y	z	Uiso*/Ueq
Cu1	0.50430 (12)	0.54334 (8)	0.25843 (4)	0.03442 (15)
S1	0.7793 (3)	0.26210 (11)	0.15869 (12)	0.0543 (5)
S2	0.2363 (3)	0.82615 (11)	0.34351 (12)	0.0583 (5)
N1	0.2789 (7)	0.4510 (3)	0.2305 (2)	0.0254 (9)
H1	0.1630	0.4766	0.2476	0.030*
N2	0.3528 (7)	0.3783 (3)	0.3734 (3)	0.0274 (10)
N3	0.5658 (7)	0.5102 (3)	0.3877 (2)	0.0303 (11)
H3	0.4650	0.5373	0.4146	0.036*
N4	0.7316 (7)	0.6346 (3)	0.2878 (2)	0.0273 (10)
H4	0.8493	0.6078	0.2736	0.033*
N5	0.6763 (8)	0.7003 (3)	0.1436 (3)	0.0342 (11)
N6	0.4452 (7)	0.5748 (3)	0.1283 (2)	0.0294 (11)
H6	0.5388	0.5424	0.1015	0.035*
N7	0.7810 (9)	0.4420 (4)	0.2165 (3)	0.0486 (14)
N8	0.2189 (8)	0.6434 (4)	0.2945 (3)	0.0484 (14)
C1	0.3104 (9)	0.3626 (4)	0.2767 (3)	0.0297 (12)
H1A	0.1858	0.3246	0.2609	0.036*
H1B	0.4275	0.3303	0.2582	0.036*
C2	0.5574 (9)	0.4111 (4)	0.4052 (3)	0.0339 (13)
H2A	0.6567	0.3789	0.3746	0.041*
H2B	0.5953	0.3994	0.4697	0.041*
C3	0.7627 (7)	0.5530 (5)	0.4258 (3)	0.0288 (12)
H3A	0.8787	0.5158	0.4127	0.035*
H3B	0.7747	0.5582	0.4910	0.035*
C4	0.7689 (9)	0.6463 (4)	0.3847 (3)	0.0359 (14)
H4A	0.6618	0.6857	0.4027	0.043*
H4B	0.9049	0.6748	0.4047	0.043*
C5	0.7015 (10)	0.7205 (4)	0.2374 (3)	0.0341 (13)
H5A	0.5780	0.7522	0.2505	0.041*
H5B	0.8222	0.7605	0.2549	0.041*
C6	0.4694 (9)	0.6717 (4)	0.1056 (3)	0.0345 (13)
H6A	0.4461	0.6794	0.0403	0.041*
H6B	0.3674	0.7091	0.1298	0.041*
C7	0.2393 (8)	0.5371 (5)	0.0934 (3)	0.0348 (12)
H7A	0.2174	0.5339	0.0278	0.042*
H7B	0.1307	0.5758	0.1111	0.042*
C8	0.2317 (9)	0.4425 (4)	0.1326 (3)	0.0311 (12)
H8A	0.0933	0.4158	0.1142	0.037*
H8B	0.3339	0.4027	0.1115	0.037*
C9	0.2883 (9)	0.3009 (4)	0.4249 (3)	0.0361 (13)
H9	0.3499	0.3132	0.4883	0.043*
C10	0.3729 (9)	0.2099 (3)	0.4034 (3)	0.0331 (13)
C11	0.2610 (11)	0.1501 (5)	0.3414 (4)	0.0534 (18)
H11	0.1285	0.1674	0.3112	0.064*
C12	0.3396 (14)	0.0674 (5)	0.3239 (4)	0.066 (2)
H12	0.2606	0.0278	0.2824	0.079*
C13	0.5321 (13)	0.0415 (7)	0.3659 (4)	0.0688 (19)
H13	0.5858	−0.0158	0.3530	0.083*
C14	0.6468 (11)	0.0979 (5)	0.4265 (4)	0.0541 (18)
H14	0.7794	0.0797	0.4558	0.065*
C15	0.5689 (9)	0.1810 (4)	0.4445 (4)	0.0402 (14)
H15	0.6501	0.2199	0.4860	0.048*
C16	0.0579 (8)	0.3032 (4)	0.4214 (4)	0.0473 (15)
H16A	−0.0116	0.3002	0.3594	0.071*
H16B	0.0197	0.3595	0.4483	0.071*
H16C	0.0163	0.2513	0.4542	0.071*
C17	0.7789 (9)	0.7675 (4)	0.0932 (3)	0.0380 (14)
H17	0.9250	0.7709	0.1244	0.046*
C18	0.6930 (9)	0.8627 (4)	0.0969 (3)	0.0390 (14)
C19	0.8066 (12)	0.9284 (5)	0.1483 (4)	0.059 (2)
H19	0.9418	0.9143	0.1778	0.071*
C20	0.7286 (15)	1.0139 (5)	0.1579 (4)	0.074 (3)
H20	0.8100	1.0583	0.1928	0.089*
C21	0.5318 (14)	1.0343 (6)	0.1165 (4)	0.070 (2)
H21	0.4761	1.0925	0.1243	0.084*
C22	0.4137 (12)	0.9710 (5)	0.0634 (4)	0.060 (2)
H22	0.2793	0.9855	0.0334	0.072*
C23	0.4972 (10)	0.8857 (4)	0.0553 (4)	0.0453 (16)
H23	0.4166	0.8415	0.0198	0.054*
C24	0.7881 (9)	0.7340 (4)	0.0004 (3)	0.0456 (14)
H24A	0.8273	0.6699	0.0028	0.068*
H24B	0.8902	0.7693	−0.0246	0.068*
H24C	0.6527	0.7411	−0.0371	0.068*
C25	0.7772 (9)	0.3680 (5)	0.1908 (4)	0.0360 (14)
C26	0.2274 (9)	0.7192 (4)	0.3148 (4)	0.0368 (14)

	U11	U22	U33	U12	U13	U23
Cu1	0.0461 (3)	0.0263 (2)	0.0280 (3)	−0.0102 (3)	−0.0019 (2)	0.0032 (3)
S1	0.0567 (12)	0.0369 (10)	0.0655 (11)	−0.0006 (9)	−0.0005 (9)	−0.0091 (8)
S2	0.0683 (13)	0.0330 (10)	0.0674 (11)	−0.0024 (9)	−0.0058 (9)	−0.0068 (8)
N1	0.029 (2)	0.020 (2)	0.028 (2)	−0.0074 (19)	0.0044 (17)	−0.0053 (16)
N2	0.027 (2)	0.024 (2)	0.031 (2)	−0.0027 (19)	0.0019 (18)	0.0087 (17)
N3	0.035 (3)	0.027 (2)	0.029 (2)	−0.004 (2)	0.0039 (18)	−0.0033 (16)
N4	0.029 (2)	0.023 (2)	0.029 (2)	−0.008 (2)	0.0031 (17)	−0.0032 (18)
N5	0.041 (3)	0.033 (3)	0.028 (2)	−0.008 (2)	0.004 (2)	0.0076 (19)
N6	0.040 (3)	0.023 (2)	0.0237 (19)	−0.003 (2)	0.0022 (18)	−0.0013 (15)
N7	0.048 (4)	0.036 (3)	0.062 (3)	0.007 (3)	0.012 (3)	−0.007 (3)
N8	0.047 (4)	0.034 (3)	0.063 (3)	0.001 (3)	0.009 (3)	−0.009 (3)
C1	0.039 (3)	0.020 (3)	0.031 (3)	−0.008 (2)	0.008 (2)	0.002 (2)
C2	0.041 (3)	0.023 (3)	0.033 (3)	0.003 (3)	−0.005 (2)	0.011 (2)
C3	0.031 (3)	0.028 (3)	0.026 (2)	−0.001 (3)	−0.0013 (18)	−0.003 (2)
C4	0.043 (4)	0.039 (3)	0.024 (2)	−0.004 (3)	0.002 (2)	−0.002 (2)
C5	0.042 (4)	0.025 (3)	0.033 (3)	−0.006 (3)	0.002 (2)	0.004 (2)
C6	0.039 (3)	0.033 (3)	0.031 (3)	−0.006 (3)	0.004 (2)	0.008 (2)
C7	0.041 (3)	0.039 (3)	0.0217 (19)	−0.007 (3)	−0.0029 (18)	−0.001 (3)
C8	0.040 (3)	0.026 (3)	0.027 (2)	0.001 (3)	0.006 (2)	−0.001 (2)
C9	0.041 (3)	0.036 (3)	0.033 (3)	0.002 (3)	0.010 (2)	0.015 (2)
C10	0.041 (3)	0.021 (3)	0.038 (3)	−0.004 (2)	0.009 (2)	0.008 (2)
C11	0.064 (5)	0.040 (4)	0.050 (4)	−0.008 (3)	−0.006 (3)	0.011 (3)
C12	0.097 (6)	0.041 (4)	0.056 (4)	−0.009 (4)	0.005 (4)	−0.005 (3)
C13	0.099 (6)	0.045 (4)	0.068 (4)	0.008 (5)	0.029 (4)	0.000 (5)
C14	0.051 (4)	0.043 (4)	0.073 (4)	0.014 (3)	0.023 (3)	0.011 (3)
C15	0.029 (3)	0.041 (3)	0.050 (3)	0.003 (3)	0.007 (3)	0.007 (3)
C16	0.027 (3)	0.059 (4)	0.056 (4)	−0.003 (3)	0.009 (3)	0.021 (3)
C17	0.050 (4)	0.025 (3)	0.040 (3)	−0.003 (3)	0.010 (3)	0.005 (2)
C18	0.050 (4)	0.032 (3)	0.035 (3)	−0.003 (3)	0.007 (3)	0.008 (2)
C19	0.091 (6)	0.031 (3)	0.048 (4)	−0.009 (4)	−0.007 (4)	0.007 (3)
C20	0.123 (8)	0.042 (4)	0.050 (4)	−0.005 (4)	−0.009 (4)	0.001 (3)
C21	0.131 (7)	0.026 (3)	0.058 (4)	0.002 (5)	0.029 (4)	0.000 (4)
C22	0.077 (5)	0.046 (4)	0.059 (4)	0.021 (4)	0.021 (4)	0.018 (3)
C23	0.056 (4)	0.032 (3)	0.051 (3)	0.004 (3)	0.018 (3)	0.009 (3)
C24	0.058 (4)	0.040 (3)	0.044 (3)	0.002 (3)	0.022 (3)	0.007 (3)
C25	0.032 (3)	0.042 (4)	0.033 (3)	0.004 (3)	0.003 (2)	0.005 (3)
C26	0.033 (3)	0.037 (4)	0.040 (3)	0.005 (3)	0.005 (3)	0.004 (3)

Cu1—N3	2.008 (4)	C6—H6B	0.9900
Cu1—N4	2.008 (4)	C7—C8	1.523 (9)
Cu1—N1	2.008 (4)	C7—H7A	0.9900
Cu1—N6	2.014 (4)	C7—H7B	0.9900
Cu1—N7	2.527 (6)	C8—H8A	0.9900
Cu1—N8	2.528 (6)	C8—H8B	0.9900
S1—C25	1.639 (7)	C9—C16	1.512 (7)
S2—C26	1.636 (7)	C9—C10	1.513 (8)
N1—C8	1.480 (6)	C9—H9	1.0000
N1—C1	1.482 (6)	C10—C15	1.403 (7)
N1—H1	0.9300	C10—C11	1.406 (8)
N2—C2	1.437 (7)	C11—C12	1.372 (10)
N2—C1	1.474 (6)	C11—H11	0.9500
N2—C9	1.490 (6)	C12—C13	1.375 (10)
N3—C3	1.470 (7)	C12—H12	0.9500
N3—C2	1.490 (6)	C13—C14	1.372 (10)
N3—H3	0.9300	C13—H13	0.9500
N4—C4	1.469 (6)	C14—C15	1.376 (8)
N4—C5	1.479 (7)	C14—H14	0.9500
N4—H4	0.9300	C15—H15	0.9500
N5—C5	1.445 (6)	C16—H16A	0.9800
N5—C6	1.450 (7)	C16—H16B	0.9800
N5—C17	1.490 (7)	C16—H16C	0.9800
N6—C7	1.480 (7)	C17—C24	1.514 (7)
N6—C6	1.487 (7)	C17—C18	1.520 (8)
N6—H6	0.9300	C17—H17	1.0000
N7—C25	1.160 (8)	C18—C23	1.379 (8)
N8—C26	1.160 (8)	C18—C19	1.384 (9)
C1—H1A	0.9900	C19—C20	1.381 (10)
C1—H1B	0.9900	C19—H19	0.9500
C2—H2A	0.9900	C20—C21	1.376 (11)
C2—H2B	0.9900	C20—H20	0.9500
C3—C4	1.518 (8)	C21—C22	1.385 (11)
C3—H3A	0.9900	C21—H21	0.9500
C3—H3B	0.9900	C22—C23	1.389 (9)
C4—H4A	0.9900	C22—H22	0.9500
C4—H4B	0.9900	C23—H23	0.9500
C5—H5A	0.9900	C24—H24A	0.9800
C5—H5B	0.9900	C24—H24B	0.9800
C6—H6A	0.9900	C24—H24C	0.9800
N3—Cu1—N4	85.80 (17)	N6—C7—H7A	110.3
N3—Cu1—N1	93.45 (17)	C8—C7—H7A	110.3
N4—Cu1—N1	179.2 (2)	N6—C7—H7B	110.3
N3—Cu1—N6	179.1 (2)	C8—C7—H7B	110.3
N4—Cu1—N6	94.36 (17)	H7A—C7—H7B	108.6
N1—Cu1—N6	86.38 (17)	N1—C8—C7	107.8 (4)
C8—N1—C1	113.3 (4)	N1—C8—H8A	110.2
C8—N1—Cu1	106.9 (3)	C7—C8—H8A	110.2
C1—N1—Cu1	117.3 (3)	N1—C8—H8B	110.2
C8—N1—H1	106.2	C7—C8—H8B	110.2
C1—N1—H1	106.2	H8A—C8—H8B	108.5
Cu1—N1—H1	106.2	N2—C9—C16	110.0 (4)
C2—N2—C1	113.3 (4)	N2—C9—C10	114.6 (4)
C2—N2—C9	114.7 (4)	C16—C9—C10	114.7 (5)
C1—N2—C9	112.7 (4)	N2—C9—H9	105.6
C3—N3—C2	114.1 (4)	C16—C9—H9	105.6
C3—N3—Cu1	107.4 (3)	C10—C9—H9	105.6
C2—N3—Cu1	114.1 (3)	C15—C10—C11	116.6 (6)
C3—N3—H3	106.9	C15—C10—C9	121.2 (5)
C2—N3—H3	106.9	C11—C10—C9	122.2 (5)
Cu1—N3—H3	106.9	C12—C11—C10	121.2 (7)
C4—N4—C5	114.1 (4)	C12—C11—H11	119.4
C4—N4—Cu1	107.1 (3)	C10—C11—H11	119.4
C5—N4—Cu1	115.5 (3)	C11—C12—C13	120.5 (7)
C4—N4—H4	106.5	C11—C12—H12	119.8
C5—N4—H4	106.5	C13—C12—H12	119.8
Cu1—N4—H4	106.5	C14—C13—C12	120.2 (8)
C5—N5—C6	113.4 (5)	C14—C13—H13	119.9
C5—N5—C17	113.0 (4)	C12—C13—H13	119.9
C6—N5—C17	117.8 (4)	C13—C14—C15	119.7 (7)
C7—N6—C6	114.0 (5)	C13—C14—H14	120.2
C7—N6—Cu1	106.2 (3)	C15—C14—H14	120.2
C6—N6—Cu1	116.2 (3)	C14—C15—C10	121.9 (6)
C7—N6—H6	106.6	C14—C15—H15	119.0
C6—N6—H6	106.6	C10—C15—H15	119.0
Cu1—N6—H6	106.6	C9—C16—H16A	109.5
N2—C1—N1	109.0 (4)	C9—C16—H16B	109.5
N2—C1—H1A	109.9	H16A—C16—H16B	109.5
N1—C1—H1A	109.9	C9—C16—H16C	109.5
N2—C1—H1B	109.9	H16A—C16—H16C	109.5
N1—C1—H1B	109.9	H16B—C16—H16C	109.5
H1A—C1—H1B	108.3	N5—C17—C24	111.2 (4)
N2—C2—N3	109.4 (4)	N5—C17—C18	113.0 (5)
N2—C2—H2A	109.8	C24—C17—C18	114.4 (4)
N3—C2—H2A	109.8	N5—C17—H17	105.8
N2—C2—H2B	109.8	C24—C17—H17	105.8
N3—C2—H2B	109.8	C18—C17—H17	105.8
H2A—C2—H2B	108.2	C23—C18—C19	117.5 (6)
N3—C3—C4	108.1 (4)	C23—C18—C17	122.4 (6)
N3—C3—H3A	110.1	C19—C18—C17	120.0 (6)
C4—C3—H3A	110.1	C20—C19—C18	121.7 (7)
N3—C3—H3B	110.1	C20—C19—H19	119.2
C4—C3—H3B	110.1	C18—C19—H19	119.2
H3A—C3—H3B	108.4	C21—C20—C19	119.4 (7)
N4—C4—C3	107.3 (4)	C21—C20—H20	120.3
N4—C4—H4A	110.2	C19—C20—H20	120.3
C3—C4—H4A	110.2	C20—C21—C22	120.8 (7)
N4—C4—H4B	110.2	C20—C21—H21	119.6
C3—C4—H4B	110.2	C22—C21—H21	119.6
H4A—C4—H4B	108.5	C21—C22—C23	118.2 (7)
N5—C5—N4	108.8 (4)	C21—C22—H22	120.9
N5—C5—H5A	109.9	C23—C22—H22	120.9
N4—C5—H5A	109.9	C18—C23—C22	122.4 (7)
N5—C5—H5B	109.9	C18—C23—H23	118.8
N4—C5—H5B	109.9	C22—C23—H23	118.8
H5A—C5—H5B	108.3	C17—C24—H24A	109.5
N5—C6—N6	108.5 (4)	C17—C24—H24B	109.5
N5—C6—H6A	110.0	H24A—C24—H24B	109.5
N6—C6—H6A	110.0	C17—C24—H24C	109.5
N5—C6—H6B	110.0	H24A—C24—H24C	109.5
N6—C6—H6B	110.0	H24B—C24—H24C	109.5
H6A—C6—H6B	108.4	N7—C25—S1	177.3 (6)
N6—C7—C8	107.1 (4)	N8—C26—S2	179.3 (6)
N3—Cu1—N1—C8	−166.4 (3)	C6—N6—C7—C8	−172.6 (4)
N6—Cu1—N1—C8	12.7 (3)	Cu1—N6—C7—C8	−43.4 (5)
N3—Cu1—N1—C1	−38.0 (4)	C1—N1—C8—C7	−170.5 (4)
N6—Cu1—N1—C1	141.1 (4)	Cu1—N1—C8—C7	−39.7 (5)
N4—Cu1—N3—C3	−12.5 (4)	N6—C7—C8—N1	56.3 (6)
N1—Cu1—N3—C3	167.1 (4)	C2—N2—C9—C16	150.3 (5)
N4—Cu1—N3—C2	−140.0 (4)	C1—N2—C9—C16	−78.0 (6)
N1—Cu1—N3—C2	39.6 (4)	C2—N2—C9—C10	−78.8 (6)
N3—Cu1—N4—C4	−16.9 (4)	C1—N2—C9—C10	52.9 (6)
N6—Cu1—N4—C4	164.0 (4)	N2—C9—C10—C15	84.8 (6)
N3—Cu1—N4—C5	−145.2 (4)	C16—C9—C10—C15	−146.6 (5)
N6—Cu1—N4—C5	35.7 (4)	N2—C9—C10—C11	−95.1 (6)
N4—Cu1—N6—C7	−162.9 (4)	C16—C9—C10—C11	33.5 (7)
N1—Cu1—N6—C7	17.4 (4)	C15—C10—C11—C12	1.1 (9)
N4—Cu1—N6—C6	−35.0 (4)	C9—C10—C11—C12	−179.1 (6)
N1—Cu1—N6—C6	145.4 (4)	C10—C11—C12—C13	−0.9 (11)
C2—N2—C1—N1	−75.4 (6)	C11—C12—C13—C14	0.5 (11)
C9—N2—C1—N1	152.3 (4)	C12—C13—C14—C15	−0.5 (11)
C8—N1—C1—N2	−179.1 (4)	C13—C14—C15—C10	0.7 (10)
Cu1—N1—C1—N2	55.6 (5)	C11—C10—C15—C14	−1.0 (9)
C1—N2—C2—N3	80.1 (5)	C9—C10—C15—C14	179.1 (5)
C9—N2—C2—N3	−148.6 (4)	C5—N5—C17—C24	168.0 (5)
C3—N3—C2—N2	174.0 (4)	C6—N5—C17—C24	−56.7 (7)
Cu1—N3—C2—N2	−62.0 (5)	C5—N5—C17—C18	−61.8 (6)
C2—N3—C3—C4	166.4 (4)	C6—N5—C17—C18	73.6 (6)
Cu1—N3—C3—C4	38.9 (5)	N5—C17—C18—C23	−68.8 (7)
C5—N4—C4—C3	171.2 (4)	C24—C17—C18—C23	59.8 (7)
Cu1—N4—C4—C3	42.1 (5)	N5—C17—C18—C19	106.6 (6)
N3—C3—C4—N4	−54.6 (6)	C24—C17—C18—C19	−124.8 (6)
C6—N5—C5—N4	81.0 (6)	C23—C18—C19—C20	−0.1 (10)
C17—N5—C5—N4	−141.6 (5)	C17—C18—C19—C20	−175.8 (6)
C4—N4—C5—N5	177.3 (5)	C18—C19—C20—C21	1.0 (11)
Cu1—N4—C5—N5	−58.0 (6)	C19—C20—C21—C22	−1.8 (11)
C5—N5—C6—N6	−79.4 (5)	C20—C21—C22—C23	1.8 (10)
C17—N5—C6—N6	145.4 (5)	C19—C18—C23—C22	0.2 (9)
C7—N6—C6—N5	179.9 (4)	C17—C18—C23—C22	175.7 (5)
Cu1—N6—C6—N5	55.9 (6)	C21—C22—C23—C18	−1.0 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7i	0.93	2.54	3.258 (7)	135
N4—H4···N8ii	0.93	2.46	3.202 (7)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N7i	0.93	2.54	3.258 (7)	135
N4—H4⋯N8ii	0.93	2.46	3.202 (7)	137

Symmetry codes: (i) ; (ii) .