catena-Poly[[[{1-[(E)-phenyl(pyridin-2-yl-κN)methylidene]semicarbazidato-κ(2)N(1),O}copper(II)]-μ-dicyanamido-κ(2)N(1):N(5)] monohydrate].

The Cu(II) atoms in the title coordination polymer, {[Cu(C(13)H(11)N(4)O)(C(2)N(3))]·H(2)O}(n), are N,N',O-chelated by the deprotonated Schiff base ligands, and adjacent metal atoms are bridged by the dicyanamide ions, generating a polymeric chain that propagates along the b axis. The two independent metal atoms show a square-pyramidal N(4)O coordination. The two independent water mol-ecules are disordered over two positions; each water mol-ecule is a hydrogen-bond donor to a carbonyl O atom. Weak N-H⋯N hydrogen bonding is also observed.

Related literature

For the synthesis of the Schiff base ligand, see: de Lima et al. (2008 ▶). For a related copper(II) derivative, see: Peŕez-Rebolledo et al. (2006 ▶).

Experimental

Crystal data

[Cu(C13H11N4O)(C2N3)]·H2O

M = 386.86

Orthorhombic,

a = 12.3996 (2) Å

b = 21.0115 (4) Å

c = 26.7059 (5) Å

V = 6957.8 (2) Å3

Z = 16

Mo Kα radiation

μ = 1.28 mm−1

T = 293 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.629, T max = 0.784

110924 measured reflections

7982 independent reflections

5027 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.166

S = 1.12

7982 reflections

457 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035283/xu5601sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035283/xu5601Isup2.hkl

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

[Cu(C13H11N4O)(C2N3)]·H2O	F(000) = 3152
Mr = 386.86	Dx = 1.477 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9967 reflections
a = 12.3996 (2) Å	θ = 2.7–26.5°
b = 21.0115 (4) Å	µ = 1.28 mm−1
c = 26.7059 (5) Å	T = 293 K
V = 6957.8 (2) Å3	Prim, green
Z = 16	0.40 × 0.30 × 0.20 mm

Bruker Kappa APEXII diffractometer	7982 independent reflections
Radiation source: fine-focus sealed tube	5027 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→14
Tmin = 0.629, Tmax = 0.784	k = −27→27
110924 measured reflections	l = −34→34

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0668P)2 + 9.8211P] where P = (Fo2 + 2Fc2)/3
7982 reflections	(Δ/σ)max = 0.001
457 parameters	Δρmax = 0.80 e Å−3
12 restraints	Δρmin = −0.46 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.74889 (4)	0.32160 (2)	0.591725 (16)	0.03950 (15)
Cu2	0.51236 (4)	0.06952 (2)	0.406562 (15)	0.03717 (15)
O1	0.6417 (2)	0.38125 (13)	0.61888 (10)	0.0541 (8)
O2	0.6166 (2)	0.13248 (12)	0.38040 (10)	0.0489 (7)
O1W	0.4729 (16)	0.4332 (10)	0.5571 (8)	0.269 (7)	0.50
H1W1	0.5266	0.4228	0.5745	0.404*
H1W2	0.4808	0.4710	0.5475	0.404*
O2W	0.8427 (16)	0.1463 (9)	0.4332 (7)	0.234 (6)	0.50
H2W1	0.7879	0.1336	0.4177	0.280*
H2W2	0.8367	0.1858	0.4373	0.280*
O1W'	0.4691 (17)	0.5292 (11)	0.5296 (8)	0.269 (7)	0.50
O2W'	0.7929 (19)	0.1888 (10)	0.4402 (8)	0.234 (6)	0.50
N1	0.8834 (3)	0.26882 (16)	0.58984 (12)	0.0469 (8)
N2	0.7736 (3)	0.31179 (14)	0.66329 (11)	0.0362 (7)
N3	0.7020 (3)	0.33965 (15)	0.69487 (11)	0.0419 (7)
N4	0.5629 (3)	0.41008 (19)	0.69133 (14)	0.0644 (11)
H41	0.5184	0.4351	0.6749	0.077*
H42	0.5586	0.4073	0.7241	0.077*
N5	0.3807 (3)	0.01320 (15)	0.40768 (10)	0.0396 (7)
N6	0.4882 (2)	0.06112 (14)	0.33509 (11)	0.0358 (7)
N7	0.5555 (3)	0.09307 (15)	0.30382 (11)	0.0394 (7)
N8	0.6909 (3)	0.16608 (17)	0.30793 (13)	0.0555 (9)
H81	0.7353	0.1909	0.3246	0.067*
H82	0.6936	0.1649	0.2750	0.067*
N9	0.6399 (4)	0.2399 (2)	0.58076 (14)	0.0683 (12)
N10	0.5250 (4)	0.1525 (2)	0.55530 (14)	0.0735 (13)
N11	0.5158 (3)	0.09809 (17)	0.47568 (12)	0.0497 (8)
N12	0.7496 (3)	0.35269 (18)	0.52272 (13)	0.0509 (9)
N13	0.7622 (4)	0.3993 (2)	0.43995 (14)	0.0799 (15)
N14	0.8717 (3)	0.48903 (18)	0.41363 (13)	0.0539 (9)
C1	0.9380 (4)	0.2496 (2)	0.54957 (17)	0.0673 (14)
H1	0.9131	0.2611	0.5180	0.081*
C2	1.0297 (5)	0.2132 (3)	0.5532 (2)	0.0814 (18)
H2	1.0658	0.1998	0.5246	0.098*
C3	1.0669 (5)	0.1972 (2)	0.6000 (2)	0.0747 (16)
H3	1.1305	0.1741	0.6035	0.090*
C4	1.0095 (4)	0.2154 (2)	0.64189 (17)	0.0546 (11)
H4	1.0326	0.2039	0.6737	0.066*
C5	0.9172 (3)	0.25110 (17)	0.63568 (14)	0.0419 (9)
C6	0.8486 (3)	0.27313 (16)	0.67749 (13)	0.0360 (8)
C7	0.8605 (3)	0.24717 (17)	0.72905 (13)	0.0384 (8)
C8	0.7886 (4)	0.2016 (2)	0.74534 (17)	0.0546 (11)
H8	0.7321	0.1890	0.7247	0.066*
C9	0.8002 (5)	0.1745 (2)	0.7924 (2)	0.0696 (14)
H9	0.7519	0.1436	0.8032	0.084*
C10	0.8835 (5)	0.1935 (3)	0.82286 (19)	0.0758 (16)
H10	0.8909	0.1758	0.8546	0.091*
C11	0.9552 (5)	0.2379 (3)	0.80682 (19)	0.0831 (17)
H11	1.0119	0.2504	0.8275	0.100*
C12	0.9440 (4)	0.2645 (2)	0.76020 (17)	0.0653 (13)
H12	0.9937	0.2947	0.7494	0.078*
C13	0.6370 (3)	0.37643 (18)	0.66655 (14)	0.0427 (9)
C14	0.3281 (4)	−0.0096 (2)	0.44722 (15)	0.0527 (11)
H14	0.3484	0.0040	0.4790	0.063*
C15	0.2455 (4)	−0.0522 (3)	0.44297 (19)	0.0741 (16)
H15	0.2098	−0.0671	0.4713	0.089*
C16	0.2161 (5)	−0.0725 (3)	0.3959 (2)	0.0832 (18)
H16	0.1602	−0.1016	0.3920	0.100*
C17	0.2703 (4)	−0.0494 (2)	0.35449 (17)	0.0626 (13)
H17	0.2513	−0.0627	0.3225	0.075*
C18	0.3520 (3)	−0.00673 (18)	0.36126 (13)	0.0403 (8)
C19	0.4168 (3)	0.02092 (17)	0.32052 (13)	0.0368 (8)
C20	0.4045 (3)	−0.00038 (17)	0.26745 (13)	0.0369 (8)
C21	0.3209 (4)	0.0214 (2)	0.23788 (15)	0.0562 (11)
H21	0.2697	0.0492	0.2508	0.067*
C22	0.3144 (4)	0.0011 (3)	0.18867 (17)	0.0664 (13)
H22	0.2580	0.0154	0.1687	0.080*
C23	0.3888 (4)	−0.0392 (2)	0.16898 (16)	0.0644 (14)
H23	0.3844	−0.0514	0.1356	0.077*
C24	0.4709 (4)	−0.0618 (2)	0.19901 (19)	0.0647 (14)
H24	0.5207	−0.0906	0.1862	0.078*
C25	0.4789 (4)	−0.0417 (2)	0.24776 (17)	0.0521 (10)
H25	0.5354	−0.0562	0.2676	0.062*
C26	0.6197 (3)	0.13029 (17)	0.33247 (14)	0.0409 (9)
C27	0.5897 (4)	0.1987 (2)	0.56680 (14)	0.0471 (10)
C28	0.5253 (3)	0.12554 (19)	0.51235 (14)	0.0447 (9)
C29	0.7585 (3)	0.3768 (2)	0.48527 (16)	0.0483 (10)
C30	0.8225 (3)	0.4478 (2)	0.42797 (13)	0.0455 (10)

	U11	U22	U33	U12	U13	U23
Cu1	0.0501 (3)	0.0411 (3)	0.0272 (2)	−0.00041 (19)	0.00001 (19)	−0.00053 (18)
Cu2	0.0476 (3)	0.0394 (3)	0.0245 (2)	−0.0023 (2)	−0.00390 (18)	−0.00204 (17)
O1	0.070 (2)	0.0597 (18)	0.0327 (14)	0.0195 (15)	−0.0050 (13)	0.0012 (12)
O2	0.0662 (19)	0.0471 (16)	0.0334 (14)	−0.0157 (14)	−0.0080 (13)	−0.0001 (11)
O1W	0.220 (9)	0.323 (11)	0.266 (10)	0.038 (8)	−0.025 (8)	−0.002 (8)
O2W	0.247 (10)	0.253 (11)	0.201 (8)	0.037 (8)	−0.069 (8)	−0.052 (8)
O1W'	0.220 (9)	0.323 (11)	0.266 (10)	0.038 (8)	−0.025 (8)	−0.002 (8)
O2W'	0.247 (10)	0.253 (11)	0.201 (8)	0.037 (8)	−0.069 (8)	−0.052 (8)
N1	0.059 (2)	0.0457 (18)	0.0354 (17)	0.0038 (16)	0.0107 (15)	0.0022 (14)
N2	0.0452 (18)	0.0354 (16)	0.0281 (14)	0.0019 (14)	−0.0007 (13)	−0.0020 (12)
N3	0.046 (2)	0.0472 (18)	0.0323 (16)	0.0081 (15)	−0.0028 (14)	−0.0045 (14)
N4	0.075 (3)	0.078 (3)	0.0401 (19)	0.036 (2)	0.0021 (18)	0.0022 (18)
N5	0.0458 (19)	0.0448 (17)	0.0282 (15)	−0.0011 (14)	0.0010 (13)	0.0004 (13)
N6	0.0418 (18)	0.0395 (17)	0.0261 (14)	−0.0010 (13)	−0.0031 (12)	−0.0002 (12)
N7	0.0487 (19)	0.0429 (17)	0.0266 (14)	−0.0060 (15)	−0.0046 (13)	0.0028 (13)
N8	0.070 (3)	0.054 (2)	0.0427 (19)	−0.0245 (19)	−0.0014 (17)	0.0026 (16)
N9	0.090 (3)	0.063 (2)	0.052 (2)	−0.027 (2)	0.001 (2)	−0.0150 (19)
N10	0.097 (3)	0.082 (3)	0.041 (2)	−0.045 (3)	0.021 (2)	−0.029 (2)
N11	0.062 (2)	0.055 (2)	0.0321 (17)	−0.0067 (17)	−0.0025 (15)	−0.0054 (15)
N12	0.058 (2)	0.056 (2)	0.0389 (19)	−0.0099 (17)	0.0001 (16)	0.0063 (16)
N13	0.100 (3)	0.096 (3)	0.043 (2)	−0.056 (3)	−0.028 (2)	0.030 (2)
N14	0.061 (2)	0.058 (2)	0.0425 (19)	−0.0145 (19)	−0.0045 (17)	0.0155 (16)
C1	0.089 (4)	0.068 (3)	0.044 (2)	0.022 (3)	0.027 (2)	0.007 (2)
C2	0.101 (4)	0.084 (4)	0.060 (3)	0.041 (3)	0.036 (3)	0.007 (3)
C3	0.079 (4)	0.069 (3)	0.076 (4)	0.035 (3)	0.031 (3)	0.011 (3)
C4	0.062 (3)	0.051 (2)	0.051 (3)	0.012 (2)	0.007 (2)	0.009 (2)
C5	0.050 (2)	0.0348 (19)	0.041 (2)	0.0007 (17)	0.0088 (17)	0.0028 (15)
C6	0.043 (2)	0.0308 (17)	0.0345 (18)	−0.0025 (16)	0.0010 (15)	0.0002 (14)
C7	0.043 (2)	0.0394 (19)	0.0326 (18)	0.0044 (16)	0.0035 (16)	0.0042 (15)
C8	0.062 (3)	0.047 (2)	0.056 (3)	−0.007 (2)	0.004 (2)	0.005 (2)
C9	0.079 (4)	0.056 (3)	0.074 (3)	−0.002 (3)	0.023 (3)	0.020 (3)
C10	0.088 (4)	0.089 (4)	0.051 (3)	0.012 (3)	0.002 (3)	0.034 (3)
C11	0.081 (4)	0.121 (5)	0.048 (3)	−0.013 (4)	−0.019 (3)	0.025 (3)
C12	0.064 (3)	0.085 (3)	0.047 (2)	−0.025 (3)	−0.011 (2)	0.016 (2)
C13	0.051 (2)	0.042 (2)	0.035 (2)	0.0092 (18)	−0.0012 (17)	−0.0034 (16)
C14	0.059 (3)	0.065 (3)	0.033 (2)	−0.002 (2)	0.0065 (19)	0.0007 (18)
C15	0.066 (3)	0.106 (4)	0.051 (3)	−0.023 (3)	0.011 (2)	0.014 (3)
C16	0.071 (4)	0.118 (5)	0.061 (3)	−0.043 (3)	−0.003 (3)	0.013 (3)
C17	0.064 (3)	0.082 (3)	0.042 (2)	−0.032 (3)	−0.006 (2)	0.003 (2)
C18	0.042 (2)	0.048 (2)	0.0305 (18)	−0.0046 (17)	−0.0027 (15)	−0.0003 (15)
C19	0.042 (2)	0.0369 (19)	0.0314 (18)	−0.0001 (16)	−0.0041 (15)	0.0008 (14)
C20	0.042 (2)	0.0375 (19)	0.0307 (18)	−0.0070 (16)	−0.0029 (15)	−0.0030 (14)
C21	0.059 (3)	0.071 (3)	0.038 (2)	0.011 (2)	−0.011 (2)	−0.008 (2)
C22	0.076 (3)	0.084 (3)	0.039 (2)	−0.002 (3)	−0.023 (2)	−0.008 (2)
C23	0.086 (4)	0.074 (3)	0.034 (2)	−0.028 (3)	0.004 (2)	−0.019 (2)
C24	0.071 (3)	0.055 (3)	0.069 (3)	−0.007 (2)	0.020 (3)	−0.032 (2)
C25	0.053 (3)	0.054 (3)	0.049 (2)	−0.001 (2)	−0.003 (2)	−0.007 (2)
C26	0.050 (2)	0.037 (2)	0.0356 (19)	0.0002 (17)	−0.0006 (17)	0.0036 (16)
C27	0.060 (3)	0.053 (2)	0.0280 (18)	−0.007 (2)	0.0055 (18)	−0.0048 (17)
C28	0.052 (2)	0.049 (2)	0.033 (2)	−0.0117 (19)	0.0037 (17)	−0.0062 (17)
C29	0.047 (2)	0.054 (2)	0.043 (2)	−0.0148 (19)	−0.0113 (18)	0.0046 (19)
C30	0.050 (2)	0.062 (3)	0.0252 (18)	−0.008 (2)	−0.0133 (17)	0.0066 (17)

Cu1—N2	1.946 (3)	C1—H1	0.9300
Cu1—N12	1.955 (3)	C2—C3	1.376 (7)
Cu1—O1	1.966 (3)	C2—H2	0.9300
Cu1—N1	2.004 (4)	C3—C4	1.380 (6)
Cu1—N9	2.205 (4)	C3—H3	0.9300
Cu2—N6	1.940 (3)	C4—C5	1.377 (6)
Cu2—N11	1.941 (3)	C4—H4	0.9300
Cu2—O2	1.977 (3)	C5—C6	1.479 (5)
Cu2—N5	2.016 (3)	C6—C7	1.488 (5)
Cu2—N14i	2.228 (4)	C7—C8	1.378 (6)
O1—C13	1.278 (4)	C7—C12	1.378 (6)
O2—C26	1.281 (4)	C8—C9	1.387 (7)
O1W—H1W1	0.8401	C8—H8	0.9300
O1W—H1W2	0.8401	C9—C10	1.375 (8)
O2W—H2W1	0.8400	C9—H9	0.9300
O2W—H2W2	0.8400	C10—C11	1.359 (8)
N1—C1	1.333 (5)	C10—H10	0.9300
N1—C5	1.346 (5)	C11—C12	1.371 (6)
N2—C6	1.292 (5)	C11—H11	0.9300
N2—N3	1.358 (4)	C12—H12	0.9300
N3—C13	1.349 (5)	C14—C15	1.364 (7)
N4—C13	1.334 (5)	C14—H14	0.9300
N4—H41	0.8800	C15—C16	1.377 (7)
N4—H42	0.8800	C15—H15	0.9300
N5—C14	1.331 (5)	C16—C17	1.383 (7)
N5—C18	1.356 (4)	C16—H16	0.9300
N6—C19	1.284 (5)	C17—C18	1.365 (6)
N6—N7	1.358 (4)	C17—H17	0.9300
N7—C26	1.353 (5)	C18—C19	1.472 (5)
N8—C26	1.332 (5)	C19—C20	1.494 (5)
N8—H81	0.8800	C20—C25	1.372 (6)
N8—H82	0.8800	C20—C21	1.381 (6)
N9—C27	1.129 (5)	C21—C22	1.384 (6)
N10—C28	1.280 (5)	C21—H21	0.9300
N10—C27	1.296 (6)	C22—C23	1.358 (7)
N11—C28	1.143 (5)	C22—H22	0.9300
N12—C29	1.127 (5)	C23—C24	1.381 (7)
N13—C29	1.300 (5)	C23—H23	0.9300
N13—C30	1.303 (6)	C24—C25	1.372 (6)
N14—C30	1.127 (5)	C24—H24	0.9300
N14—Cu2ii	2.228 (4)	C25—H25	0.9300
C1—C2	1.372 (7)
N2—Cu1—N12	163.76 (14)	N2—C6—C7	125.0 (3)
N2—Cu1—O1	79.14 (12)	C5—C6—C7	121.8 (3)
N12—Cu1—O1	97.91 (14)	C8—C7—C12	118.6 (4)
N2—Cu1—N1	80.51 (13)	C8—C7—C6	118.8 (4)
N12—Cu1—N1	99.07 (14)	C12—C7—C6	122.4 (4)
O1—Cu1—N1	157.69 (13)	C7—C8—C9	120.3 (5)
N2—Cu1—N9	98.30 (14)	C7—C8—H8	119.9
N12—Cu1—N9	97.91 (15)	C9—C8—H8	119.9
O1—Cu1—N9	97.52 (15)	C10—C9—C8	119.6 (5)
N1—Cu1—N9	94.37 (16)	C10—C9—H9	120.2
N6—Cu2—N11	165.22 (14)	C8—C9—H9	120.2
N6—Cu2—O2	79.29 (12)	C11—C10—C9	120.3 (4)
N11—Cu2—O2	96.58 (13)	C11—C10—H10	119.8
N6—Cu2—N5	80.58 (12)	C9—C10—H10	119.8
N11—Cu2—N5	100.68 (13)	C10—C11—C12	120.0 (5)
O2—Cu2—N5	158.01 (11)	C10—C11—H11	120.0
N6—Cu2—N14i	96.54 (13)	C12—C11—H11	120.0
N11—Cu2—N14i	98.04 (14)	C11—C12—C7	121.1 (4)
O2—Cu2—N14i	96.66 (13)	C11—C12—H12	119.5
N5—Cu2—N14i	94.34 (14)	C7—C12—H12	119.5
C13—O1—Cu1	110.4 (2)	O1—C13—N4	118.9 (4)
C26—O2—Cu2	110.4 (2)	O1—C13—N3	125.2 (3)
H1W1—O1W—H1W2	108.7	N4—C13—N3	115.9 (3)
H2W1—O2W—H2W2	107.9	N5—C14—C15	122.6 (4)
C1—N1—C5	119.4 (4)	N5—C14—H14	118.7
C1—N1—Cu1	127.6 (3)	C15—C14—H14	118.7
C5—N1—Cu1	112.9 (3)	C14—C15—C16	118.6 (4)
C6—N2—N3	124.0 (3)	C14—C15—H15	120.7
C6—N2—Cu1	117.9 (2)	C16—C15—H15	120.7
N3—N2—Cu1	117.5 (2)	C15—C16—C17	119.5 (5)
C13—N3—N2	106.8 (3)	C15—C16—H16	120.3
C13—N4—H41	120.0	C17—C16—H16	120.3
C13—N4—H42	120.0	C18—C17—C16	119.1 (4)
H41—N4—H42	120.0	C18—C17—H17	120.5
C14—N5—C18	119.1 (4)	C16—C17—H17	120.5
C14—N5—Cu2	128.3 (3)	N5—C18—C17	121.2 (4)
C18—N5—Cu2	112.3 (2)	N5—C18—C19	114.2 (3)
C19—N6—N7	124.2 (3)	C17—C18—C19	124.5 (3)
C19—N6—Cu2	117.7 (2)	N6—C19—C18	114.3 (3)
N7—N6—Cu2	117.7 (2)	N6—C19—C20	123.7 (3)
C26—N7—N6	107.4 (3)	C18—C19—C20	121.8 (3)
C26—N8—H81	120.0	C25—C20—C21	119.7 (4)
C26—N8—H82	120.0	C25—C20—C19	119.0 (3)
H81—N8—H82	120.0	C21—C20—C19	121.4 (3)
C27—N9—Cu1	168.1 (4)	C20—C21—C22	119.0 (4)
C28—N10—C27	122.9 (4)	C20—C21—H21	120.5
C28—N11—Cu2	166.7 (3)	C22—C21—H21	120.5
C29—N12—Cu1	170.9 (4)	C23—C22—C21	121.4 (5)
C29—N13—C30	122.2 (4)	C23—C22—H22	119.3
C30—N14—Cu2ii	164.2 (3)	C21—C22—H22	119.3
N1—C1—C2	122.2 (5)	C22—C23—C24	119.4 (4)
N1—C1—H1	118.9	C22—C23—H23	120.3
C2—C1—H1	118.9	C24—C23—H23	120.3
C1—C2—C3	118.5 (4)	C25—C24—C23	119.9 (4)
C1—C2—H2	120.7	C25—C24—H24	120.1
C3—C2—H2	120.7	C23—C24—H24	120.1
C2—C3—C4	119.7 (5)	C20—C25—C24	120.7 (4)
C2—C3—H3	120.1	C20—C25—H25	119.7
C4—C3—H3	120.1	C24—C25—H25	119.7
C5—C4—C3	118.8 (4)	O2—C26—N8	119.4 (4)
C5—C4—H4	120.6	O2—C26—N7	124.6 (3)
C3—C4—H4	120.6	N8—C26—N7	116.0 (3)
N1—C5—C4	121.2 (4)	N9—C27—N10	173.3 (5)
N1—C5—C6	114.9 (3)	N11—C28—N10	172.7 (5)
C4—C5—C6	123.9 (4)	N12—C29—N13	173.4 (5)
N2—C6—C5	112.9 (3)	N14—C30—N13	174.2 (4)
N2—Cu1—O1—C13	−7.3 (3)	C3—C4—C5—N1	−0.8 (7)
N12—Cu1—O1—C13	−171.1 (3)	C3—C4—C5—C6	179.6 (4)
N1—Cu1—O1—C13	−31.8 (5)	N3—N2—C6—C5	−178.4 (3)
N9—Cu1—O1—C13	89.8 (3)	Cu1—N2—C6—C5	10.5 (4)
N6—Cu2—O2—C26	−5.6 (3)	N3—N2—C6—C7	7.6 (6)
N11—Cu2—O2—C26	−171.2 (3)	Cu1—N2—C6—C7	−163.6 (3)
N5—Cu2—O2—C26	−29.6 (5)	N1—C5—C6—N2	−7.2 (5)
N14i—Cu2—O2—C26	89.9 (3)	C4—C5—C6—N2	172.5 (4)
N2—Cu1—N1—C1	−178.0 (4)	N1—C5—C6—C7	167.1 (3)
N12—Cu1—N1—C1	−14.5 (4)	C4—C5—C6—C7	−13.2 (6)
O1—Cu1—N1—C1	−153.6 (4)	N2—C6—C7—C8	72.8 (5)
N9—Cu1—N1—C1	84.3 (4)	C5—C6—C7—C8	−100.8 (5)
N2—Cu1—N1—C5	3.5 (3)	N2—C6—C7—C12	−110.7 (5)
N12—Cu1—N1—C5	167.1 (3)	C5—C6—C7—C12	75.7 (5)
O1—Cu1—N1—C5	28.0 (5)	C12—C7—C8—C9	0.6 (7)
N9—Cu1—N1—C5	−94.2 (3)	C6—C7—C8—C9	177.3 (4)
N12—Cu1—N2—C6	−98.0 (5)	C7—C8—C9—C10	0.3 (7)
O1—Cu1—N2—C6	−178.9 (3)	C8—C9—C10—C11	−0.9 (9)
N1—Cu1—N2—C6	−8.1 (3)	C9—C10—C11—C12	0.6 (9)
N9—Cu1—N2—C6	84.9 (3)	C10—C11—C12—C7	0.4 (9)
N12—Cu1—N2—N3	90.3 (6)	C8—C7—C12—C11	−1.0 (8)
O1—Cu1—N2—N3	9.4 (3)	C6—C7—C12—C11	−177.5 (5)
N1—Cu1—N2—N3	−179.8 (3)	Cu1—O1—C13—N4	−175.2 (3)
N9—Cu1—N2—N3	−86.8 (3)	Cu1—O1—C13—N3	5.1 (5)
C6—N2—N3—C13	180.0 (3)	N2—N3—C13—O1	2.2 (5)
Cu1—N2—N3—C13	−8.9 (4)	N2—N3—C13—N4	−177.5 (4)
N6—Cu2—N5—C14	−179.3 (4)	C18—N5—C14—C15	−0.4 (7)
N11—Cu2—N5—C14	−14.2 (4)	Cu2—N5—C14—C15	−173.8 (4)
O2—Cu2—N5—C14	−155.3 (3)	N5—C14—C15—C16	0.4 (9)
N14i—Cu2—N5—C14	84.8 (4)	C14—C15—C16—C17	−0.2 (10)
N6—Cu2—N5—C18	6.9 (3)	C15—C16—C17—C18	0.0 (9)
N11—Cu2—N5—C18	172.0 (3)	C14—N5—C18—C17	0.2 (6)
O2—Cu2—N5—C18	30.9 (5)	Cu2—N5—C18—C17	174.7 (4)
N14i—Cu2—N5—C18	−89.0 (3)	C14—N5—C18—C19	−179.1 (4)
N11—Cu2—N6—C19	−104.8 (6)	Cu2—N5—C18—C19	−4.7 (4)
O2—Cu2—N6—C19	−179.8 (3)	C16—C17—C18—N5	0.0 (8)
N5—Cu2—N6—C19	−8.7 (3)	C16—C17—C18—C19	179.2 (5)
N14i—Cu2—N6—C19	84.7 (3)	N7—N6—C19—C18	−178.9 (3)
N11—Cu2—N6—N7	82.0 (6)	Cu2—N6—C19—C18	8.4 (4)
O2—Cu2—N6—N7	7.0 (2)	N7—N6—C19—C20	5.5 (6)
N5—Cu2—N6—N7	178.1 (3)	Cu2—N6—C19—C20	−167.3 (3)
N14i—Cu2—N6—N7	−88.5 (3)	N5—C18—C19—N6	−2.1 (5)
C19—N6—N7—C26	−179.3 (3)	C17—C18—C19—N6	178.6 (4)
Cu2—N6—N7—C26	−6.6 (4)	N5—C18—C19—C20	173.7 (3)
N2—Cu1—N9—C27	−157 (2)	C17—C18—C19—C20	−5.7 (6)
N12—Cu1—N9—C27	24 (2)	N6—C19—C20—C25	74.0 (5)
O1—Cu1—N9—C27	123 (2)	C18—C19—C20—C25	−101.3 (4)
N1—Cu1—N9—C27	−76 (2)	N6—C19—C20—C21	−105.0 (5)
N6—Cu2—N11—C28	−52.0 (19)	C18—C19—C20—C21	79.7 (5)
O2—Cu2—N11—C28	20.8 (16)	C25—C20—C21—C22	−0.3 (7)
N5—Cu2—N11—C28	−145.5 (16)	C19—C20—C21—C22	178.7 (4)
N14i—Cu2—N11—C28	118.5 (16)	C20—C21—C22—C23	−0.5 (8)
C5—N1—C1—C2	−1.6 (8)	C21—C22—C23—C24	1.8 (8)
Cu1—N1—C1—C2	−179.9 (4)	C22—C23—C24—C25	−2.3 (7)
N1—C1—C2—C3	−1.0 (9)	C21—C20—C25—C24	−0.3 (6)
C1—C2—C3—C4	2.7 (9)	C19—C20—C25—C24	−179.3 (4)
C2—C3—C4—C5	−1.8 (8)	C23—C24—C25—C20	1.6 (7)
C1—N1—C5—C4	2.5 (6)	Cu2—O2—C26—N8	−175.3 (3)
Cu1—N1—C5—C4	−179.0 (3)	Cu2—O2—C26—N7	4.0 (5)
C1—N1—C5—C6	−177.8 (4)	N6—N7—C26—O2	1.5 (5)
Cu1—N1—C5—C6	0.7 (4)	N6—N7—C26—N8	−179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H42···N7iii	0.88	2.13	3.006 (5)	176
N8—H82···N3iv	0.88	2.15	3.025 (5)	179
O1w—H1w1···O1	0.84	2.05	2.88 (2)	169
O2w—H2w1···O2	0.84	2.34	3.151 (19)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H42⋯N7i	0.88	2.13	3.006 (5)	176
N8—H82⋯N3ii	0.88	2.15	3.025 (5)	179
O1w—H1w1⋯O1	0.84	2.05	2.88 (2)	169
O2w—H2w1⋯O2	0.84	2.34	3.151 (19)	161

Symmetry codes: (i) ; (ii) .