[2,6-Dioxo-1,2,3,6-tetra-hydro-pyrim-idine-4-carboxyl-ato(2-)]bis(pyrazino[2,3-f][1,10]phenanthroline)cobalt(II) dihydrate.

The title complex, [Co(C(5)H(2)N(2)O(4))(C(14)H(8)N(4))(2)]·2H(2)O, features a slightly distorted octa-hedral geometry for Co due to the sterical requirements of the orotic acid and pyrazino[2,3-f][1,10]phenanthroline ligands. Inter-molecular hydrogen bonding between the uncoordinated water mol-ecules and the ligand stablizes the structure of the complex.

Related literature

For related literature, see: Darensbourg et al. (1998 ▶); Lieberman et al. (1955 ▶); Lalioti et al. (1998 ▶).

Experimental

Crystal data

[Co(C5H2N2O4)(C14H8N4)2]·2H2O

M = 713.54

Monoclinic,

a = 15.9468 (7) Å

b = 13.3765 (6) Å

c = 15.5661 (7) Å

β = 117.5610 (10)°

V = 2943.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 293 (2) K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.903, T max = 0.938

32977 measured reflections

5185 independent reflections

4601 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.105

S = 1.00

5185 reflections

451 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.44 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064495/fi2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064495/fi2050Isup2.hkl

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

[Co(C5H2N2O4)(C14H8N4)2]·2H2O	F000 = 1460
Mr = 713.54	Dx = 1.610 Mg m−3
Monoclinic, P2(1)/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14858 reflections
a = 15.9468 (7) Å	θ = 2.6–28.1º
b = 13.3765 (6) Å	µ = 0.65 mm−1
c = 15.5661 (7) Å	T = 293 (2) K
β = 117.5610 (10)º	Block, orange
V = 2943.6 (2) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5185 independent reflections
Radiation source: sealed tube	4601 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 293(2) K	θmax = 25.0º
φ & ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.903, Tmax = 0.938	k = −15→15
32977 measured reflections	l = −18→18

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0839P)2 + 0.3838P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
5185 reflections	Δρmax = 0.30 e Å−3
451 parameters	Δρmin = −0.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Co1	0.302202 (16)	0.138211 (16)	0.366964 (15)	0.02739 (11)
O1	0.40452 (10)	0.12832 (10)	0.50951 (9)	0.0376 (3)
O2	0.43227 (10)	0.09578 (13)	0.66013 (10)	0.0538 (4)
O3	0.10352 (10)	−0.00194 (13)	0.60522 (10)	0.0557 (4)
O4	0.07356 (9)	0.08288 (12)	0.31027 (9)	0.0472 (4)
O5	0.98177 (15)	0.12594 (16)	0.76679 (18)	0.0891 (7)
H33	0.9531	0.0701	0.7512	0.107*
H34	0.9388	0.1683	0.7580	0.107*
O6	0.90804 (17)	0.18193 (17)	0.28686 (18)	0.1009 (8)
H35	0.9491	0.1518	0.2759	0.121*
H36	0.8946	0.1343	0.3145	0.121*
N1	0.22079 (10)	0.09749 (11)	0.43806 (10)	0.0287 (3)
N2	0.09212 (11)	0.04177 (12)	0.45940 (11)	0.0354 (4)
H2	0.0343	0.0305	0.4329	0.042*
N3	0.28705 (10)	0.29594 (11)	0.36494 (10)	0.0299 (3)
N4	0.42213 (10)	0.18951 (11)	0.35070 (10)	0.0299 (3)
N5	0.45316 (12)	0.60117 (12)	0.37989 (12)	0.0406 (4)
N6	0.60438 (11)	0.48810 (13)	0.38628 (11)	0.0398 (4)
N7	0.30777 (10)	−0.01439 (11)	0.33132 (10)	0.0311 (3)
N8	0.21162 (11)	0.13331 (10)	0.21056 (11)	0.0303 (3)
N9	0.17387 (14)	−0.25488 (13)	0.07249 (12)	0.0474 (4)
N10	0.08181 (13)	−0.09711 (13)	−0.05752 (12)	0.0460 (4)
C1	0.37945 (13)	0.10401 (14)	0.57318 (12)	0.0337 (4)
C2	0.27470 (12)	0.08264 (12)	0.53502 (12)	0.0295 (4)
C3	0.24123 (13)	0.04902 (14)	0.59542 (13)	0.0360 (4)
H3A	0.2820	0.0402	0.6610	0.043*
C4	0.14344 (13)	0.02734 (15)	0.55768 (13)	0.0370 (4)
C5	0.12786 (13)	0.07517 (13)	0.39814 (12)	0.0317 (4)
C6	0.21428 (14)	0.34805 (14)	0.36155 (14)	0.0353 (4)
H6	0.1630	0.3133	0.3599	0.042*
C7	0.21152 (14)	0.45158 (15)	0.36044 (14)	0.0395 (4)
H7	0.1584	0.4851	0.3556	0.047*
C8	0.28830 (14)	0.50429 (15)	0.36655 (13)	0.0363 (4)
H8	0.2888	0.5738	0.3685	0.044*
C9	0.36554 (13)	0.45180 (13)	0.36978 (12)	0.0289 (4)
C10	0.45001 (12)	0.50074 (13)	0.37630 (12)	0.0309 (4)
C11	0.53149 (17)	0.64312 (15)	0.38635 (16)	0.0468 (5)
H11	0.5365	0.7124	0.3883	0.056*
C12	0.60592 (15)	0.58649 (16)	0.39021 (15)	0.0456 (5)
H12	0.6595	0.6195	0.3959	0.055*
C13	0.52507 (13)	0.44397 (14)	0.37875 (12)	0.0310 (4)
C14	0.51799 (13)	0.33593 (14)	0.37159 (12)	0.0305 (4)
C15	0.58863 (13)	0.27483 (16)	0.37097 (14)	0.0390 (4)
H15	0.6449	0.3029	0.3782	0.047*
C16	0.57528 (14)	0.17395 (16)	0.35985 (15)	0.0419 (5)
H16	0.6222	0.1327	0.3597	0.050*
C17	0.49038 (14)	0.13382 (14)	0.34878 (14)	0.0351 (4)
H17	0.4809	0.0652	0.3397	0.042*
C18	0.43614 (12)	0.28890 (13)	0.36294 (11)	0.0266 (4)
C19	0.36096 (12)	0.34745 (13)	0.36641 (12)	0.0270 (4)
C20	0.35704 (15)	−0.08618 (14)	0.39335 (14)	0.0406 (5)
H20	0.3975	−0.0688	0.4572	0.049*
C21	0.35049 (16)	−0.18542 (15)	0.36665 (15)	0.0453 (5)
H21	0.3856	−0.2336	0.4122	0.054*
C22	0.29230 (14)	−0.21251 (14)	0.27315 (14)	0.0382 (4)
H22	0.2871	−0.2792	0.2546	0.046*
C23	0.24054 (13)	−0.13879 (12)	0.20537 (13)	0.0320 (4)
C24	0.18141 (14)	−0.15951 (14)	0.10363 (15)	0.0345 (4)
C25	0.11973 (18)	−0.26838 (17)	−0.02203 (16)	0.0560 (6)
H25	0.1120	−0.3330	−0.0466	0.067*
C26	0.07401 (19)	−0.19040 (18)	−0.08593 (16)	0.0558 (6)
H26	0.0366	−0.2050	−0.1512	0.067*
C27	0.13568 (13)	−0.08080 (14)	0.03829 (13)	0.0343 (4)
C28	0.14542 (12)	0.02137 (14)	0.07340 (12)	0.0323 (4)
C29	0.10276 (14)	0.10256 (15)	0.01198 (14)	0.0393 (4)
H29	0.0660	0.0928	−0.0543	0.047*
C30	0.11575 (15)	0.19611 (16)	0.05054 (14)	0.0441 (5)
H30	0.0887	0.2511	0.0106	0.053*
C31	0.16973 (14)	0.20886 (14)	0.15002 (13)	0.0391 (4)
H31	0.1769	0.2731	0.1754	0.047*
C32	0.20028 (12)	0.04064 (13)	0.17205 (12)	0.0276 (4)
C33	0.25063 (12)	−0.04016 (13)	0.23834 (12)	0.0276 (4)

	U11	U22	U33	U12	U13	U23
Co1	0.03091 (17)	0.02377 (17)	0.02886 (16)	−0.00288 (9)	0.01500 (12)	−0.00119 (8)
O1	0.0316 (7)	0.0471 (8)	0.0316 (7)	−0.0091 (6)	0.0124 (6)	−0.0019 (5)
O2	0.0407 (8)	0.0803 (12)	0.0311 (7)	−0.0083 (8)	0.0088 (6)	0.0007 (7)
O3	0.0465 (9)	0.0841 (12)	0.0447 (8)	−0.0048 (8)	0.0280 (7)	0.0161 (8)
O4	0.0330 (7)	0.0733 (11)	0.0317 (7)	−0.0048 (7)	0.0118 (6)	0.0063 (7)
O5	0.0666 (13)	0.0695 (13)	0.1107 (18)	−0.0005 (10)	0.0236 (12)	0.0099 (11)
O6	0.1180 (18)	0.0916 (15)	0.145 (2)	0.0530 (14)	0.1050 (17)	0.0658 (15)
N1	0.0301 (8)	0.0286 (7)	0.0285 (7)	−0.0021 (6)	0.0143 (6)	−0.0001 (6)
N2	0.0299 (8)	0.0425 (9)	0.0360 (8)	−0.0033 (7)	0.0172 (7)	0.0031 (7)
N3	0.0305 (8)	0.0281 (8)	0.0338 (8)	−0.0039 (6)	0.0173 (6)	−0.0042 (6)
N4	0.0339 (8)	0.0277 (8)	0.0309 (7)	0.0013 (6)	0.0173 (6)	0.0013 (6)
N5	0.0516 (10)	0.0265 (8)	0.0447 (9)	−0.0061 (7)	0.0233 (8)	−0.0001 (7)
N6	0.0373 (9)	0.0448 (10)	0.0393 (9)	−0.0107 (7)	0.0193 (7)	−0.0002 (7)
N7	0.0358 (8)	0.0259 (7)	0.0305 (8)	0.0013 (6)	0.0145 (6)	0.0006 (6)
N8	0.0349 (9)	0.0254 (8)	0.0308 (8)	−0.0022 (6)	0.0155 (7)	0.0006 (6)
N9	0.0634 (11)	0.0342 (9)	0.0505 (10)	−0.0090 (8)	0.0314 (9)	−0.0114 (8)
N10	0.0582 (11)	0.0467 (10)	0.0352 (9)	−0.0150 (9)	0.0233 (8)	−0.0078 (7)
C1	0.0361 (10)	0.0321 (9)	0.0296 (9)	−0.0044 (8)	0.0123 (8)	−0.0037 (7)
C2	0.0339 (9)	0.0258 (9)	0.0289 (8)	−0.0007 (7)	0.0146 (7)	−0.0022 (7)
C3	0.0391 (11)	0.0397 (10)	0.0288 (9)	−0.0008 (8)	0.0155 (8)	0.0013 (8)
C4	0.0420 (11)	0.0369 (10)	0.0380 (10)	−0.0006 (8)	0.0235 (9)	0.0038 (8)
C5	0.0336 (10)	0.0312 (9)	0.0328 (9)	−0.0005 (8)	0.0173 (8)	0.0013 (7)
C6	0.0322 (10)	0.0357 (10)	0.0440 (11)	−0.0016 (8)	0.0226 (9)	−0.0033 (8)
C7	0.0389 (11)	0.0366 (10)	0.0487 (11)	0.0072 (8)	0.0251 (9)	−0.0003 (8)
C8	0.0435 (11)	0.0275 (10)	0.0411 (11)	0.0043 (8)	0.0222 (9)	−0.0002 (7)
C9	0.0351 (10)	0.0264 (9)	0.0265 (8)	−0.0009 (7)	0.0154 (7)	−0.0009 (7)
C10	0.0387 (10)	0.0279 (9)	0.0255 (8)	−0.0049 (7)	0.0143 (7)	−0.0003 (7)
C11	0.0582 (14)	0.0322 (11)	0.0499 (12)	−0.0155 (9)	0.0251 (11)	−0.0023 (8)
C12	0.0473 (12)	0.0467 (13)	0.0448 (11)	−0.0188 (10)	0.0228 (9)	−0.0017 (9)
C13	0.0345 (10)	0.0338 (10)	0.0250 (8)	−0.0063 (7)	0.0141 (7)	−0.0001 (7)
C14	0.0313 (9)	0.0361 (10)	0.0266 (8)	0.0006 (8)	0.0154 (7)	0.0048 (7)
C15	0.0339 (10)	0.0451 (12)	0.0455 (11)	0.0006 (8)	0.0246 (9)	0.0044 (9)
C16	0.0404 (11)	0.0441 (12)	0.0510 (11)	0.0115 (9)	0.0294 (9)	0.0059 (9)
C17	0.0426 (11)	0.0308 (10)	0.0372 (10)	0.0060 (8)	0.0229 (9)	0.0009 (7)
C18	0.0307 (9)	0.0268 (9)	0.0244 (8)	−0.0003 (7)	0.0144 (7)	0.0007 (6)
C19	0.0306 (9)	0.0281 (9)	0.0228 (8)	−0.0005 (7)	0.0129 (7)	0.0008 (6)
C20	0.0464 (12)	0.0337 (10)	0.0348 (10)	0.0060 (9)	0.0129 (8)	0.0030 (8)
C21	0.0561 (13)	0.0311 (10)	0.0461 (12)	0.0106 (9)	0.0214 (10)	0.0091 (9)
C22	0.0466 (11)	0.0245 (9)	0.0466 (11)	0.0021 (8)	0.0242 (9)	−0.0001 (8)
C23	0.0353 (10)	0.0283 (10)	0.0387 (10)	−0.0041 (7)	0.0224 (9)	−0.0034 (7)
C24	0.0389 (10)	0.0335 (10)	0.0393 (10)	−0.0085 (8)	0.0250 (8)	−0.0079 (8)
C25	0.0813 (17)	0.0403 (12)	0.0524 (13)	−0.0186 (12)	0.0361 (12)	−0.0187 (10)
C26	0.0767 (16)	0.0548 (14)	0.0397 (11)	−0.0248 (12)	0.0301 (11)	−0.0182 (10)
C27	0.0387 (10)	0.0370 (10)	0.0328 (9)	−0.0106 (8)	0.0212 (8)	−0.0068 (8)
C28	0.0325 (10)	0.0343 (10)	0.0335 (9)	−0.0047 (7)	0.0182 (8)	−0.0010 (7)
C29	0.0408 (11)	0.0436 (11)	0.0301 (9)	−0.0028 (9)	0.0135 (8)	0.0015 (8)
C30	0.0506 (12)	0.0379 (11)	0.0379 (10)	0.0045 (9)	0.0155 (9)	0.0104 (8)
C31	0.0507 (12)	0.0277 (9)	0.0364 (10)	0.0000 (8)	0.0180 (9)	0.0015 (8)
C32	0.0292 (9)	0.0272 (9)	0.0296 (8)	−0.0035 (7)	0.0164 (7)	−0.0015 (7)
C33	0.0287 (9)	0.0271 (9)	0.0326 (9)	−0.0012 (7)	0.0188 (7)	−0.0004 (7)

Co1—O1	2.0622 (13)	C7—C8	1.378 (3)
Co1—N3	2.1223 (15)	C7—H7	0.9300
Co1—N7	2.1280 (15)	C8—C9	1.398 (3)
Co1—N1	2.1299 (14)	C8—H8	0.9300
Co1—N4	2.1542 (15)	C9—C19	1.397 (2)
Co1—N8	2.1827 (15)	C9—C10	1.459 (2)
O1—C1	1.271 (2)	C10—C13	1.403 (3)
O2—C1	1.224 (2)	C11—C12	1.386 (3)
O3—C4	1.242 (2)	C11—H11	0.9300
O4—C5	1.239 (2)	C12—H12	0.9300
O5—H33	0.8499	C13—C14	1.450 (3)
O5—H34	0.8500	C14—C15	1.395 (3)
O6—H35	0.8512	C14—C18	1.398 (2)
O6—H36	0.8494	C15—C16	1.365 (3)
N1—C5	1.349 (2)	C15—H15	0.9300
N1—C2	1.362 (2)	C16—C17	1.391 (3)
N2—C4	1.374 (2)	C16—H16	0.9300
N2—C5	1.392 (2)	C17—H17	0.9300
N2—H2	0.8321	C18—C19	1.454 (2)
N3—C6	1.334 (2)	C20—C21	1.380 (3)
N3—C19	1.356 (2)	C20—H20	0.9300
N4—C17	1.331 (2)	C21—C22	1.364 (3)
N4—C18	1.347 (2)	C21—H21	0.9300
N5—C11	1.330 (3)	C22—C23	1.400 (3)
N5—C10	1.345 (2)	C22—H22	0.9300
N6—C12	1.317 (3)	C23—C33	1.398 (2)
N6—C13	1.351 (2)	C23—C24	1.446 (3)
N7—C20	1.330 (2)	C24—C27	1.410 (3)
N7—C33	1.350 (2)	C25—C26	1.392 (3)
N8—C31	1.332 (2)	C25—H25	0.9300
N8—C32	1.352 (2)	C26—H26	0.9300
N9—C25	1.329 (3)	C27—C28	1.453 (3)
N9—C24	1.350 (2)	C28—C32	1.395 (2)
N10—C26	1.310 (3)	C28—C29	1.398 (3)
N10—C27	1.351 (2)	C29—C30	1.362 (3)
C1—C2	1.519 (3)	C29—H29	0.9300
C2—C3	1.355 (2)	C30—C31	1.391 (3)
C3—C4	1.419 (3)	C30—H30	0.9300
C3—H3A	0.9300	C31—H31	0.9300
C6—C7	1.385 (3)	C32—C33	1.453 (2)
C6—H6	0.9300
O1—Co1—N3	96.18 (5)	N5—C11—C12	121.89 (18)
O1—Co1—N7	96.39 (5)	N5—C11—H11	119.1
N3—Co1—N7	165.47 (5)	C12—C11—H11	119.1
O1—Co1—N1	78.09 (5)	N6—C12—C11	123.17 (19)
N3—Co1—N1	99.75 (5)	N6—C12—H12	118.4
N7—Co1—N1	89.95 (6)	C11—C12—H12	118.4
O1—Co1—N4	80.99 (5)	N6—C13—C10	121.24 (17)
N3—Co1—N4	77.45 (5)	N6—C13—C14	118.61 (16)
N7—Co1—N4	97.38 (6)	C10—C13—C14	120.15 (15)
N1—Co1—N4	158.47 (5)	C15—C14—C18	117.16 (17)
O1—Co1—N8	169.75 (6)	C15—C14—C13	123.36 (16)
N3—Co1—N8	90.07 (5)	C18—C14—C13	119.47 (16)
N7—Co1—N8	76.48 (5)	C16—C15—C14	120.07 (18)
N1—Co1—N8	108.90 (6)	C16—C15—H15	120.0
N4—Co1—N8	92.51 (6)	C14—C15—H15	120.0
C1—O1—Co1	118.54 (12)	C15—C16—C17	118.88 (18)
H33—O5—H34	104.6	C15—C16—H16	120.6
H35—O6—H36	98.3	C17—C16—H16	120.6
C5—N1—C2	118.28 (14)	N4—C17—C16	122.72 (17)
C5—N1—Co1	128.40 (11)	N4—C17—H17	118.6
C2—N1—Co1	112.90 (11)	C16—C17—H17	118.6
C4—N2—C5	125.88 (16)	N4—C18—C14	122.96 (16)
C4—N2—H2	118.6	N4—C18—C19	116.83 (15)
C5—N2—H2	115.5	C14—C18—C19	120.21 (16)
C6—N3—C19	117.94 (15)	N3—C19—C9	122.54 (16)
C6—N3—Co1	127.68 (12)	N3—C19—C18	116.80 (15)
C19—N3—Co1	114.38 (11)	C9—C19—C18	120.65 (16)
C17—N4—C18	118.16 (16)	N7—C20—C21	122.59 (18)
C17—N4—Co1	127.17 (12)	N7—C20—H20	118.7
C18—N4—Co1	113.32 (11)	C21—C20—H20	118.7
C11—N5—C10	116.12 (17)	C22—C21—C20	119.74 (18)
C12—N6—C13	115.93 (18)	C22—C21—H21	120.1
C20—N7—C33	118.21 (15)	C20—C21—H21	120.1
C20—N7—Co1	125.81 (12)	C21—C22—C23	119.32 (17)
C33—N7—Co1	115.82 (11)	C21—C22—H22	120.3
C31—N8—C32	117.49 (15)	C23—C22—H22	120.3
C31—N8—Co1	128.53 (12)	C33—C23—C22	117.41 (17)
C32—N8—Co1	113.94 (11)	C33—C23—C24	119.27 (16)
C25—N9—C24	115.47 (19)	C22—C23—C24	123.26 (16)
C26—N10—C27	116.04 (19)	N9—C24—C27	121.07 (18)
O2—C1—O1	125.55 (18)	N9—C24—C23	118.61 (18)
O2—C1—C2	119.03 (17)	C27—C24—C23	120.28 (17)
O1—C1—C2	115.41 (15)	N9—C25—C26	123.1 (2)
C3—C2—N1	124.61 (16)	N9—C25—H25	118.4
C3—C2—C1	120.41 (16)	C26—C25—H25	118.4
N1—C2—C1	114.96 (15)	N10—C26—C25	122.4 (2)
C2—C3—C4	119.40 (16)	N10—C26—H26	118.8
C2—C3—H3A	120.3	C25—C26—H26	118.8
C4—C3—H3A	120.3	N10—C27—C24	121.89 (18)
O3—C4—N2	120.15 (17)	N10—C27—C28	118.03 (17)
O3—C4—C3	125.87 (18)	C24—C27—C28	120.08 (16)
N2—C4—C3	113.98 (15)	C32—C28—C29	117.91 (17)
O4—C5—N1	123.22 (16)	C32—C28—C27	119.42 (16)
O4—C5—N2	118.98 (16)	C29—C28—C27	122.67 (16)
N1—C5—N2	117.80 (15)	C30—C29—C28	119.07 (17)
N3—C6—C7	123.02 (17)	C30—C29—H29	120.5
N3—C6—H6	118.5	C28—C29—H29	120.5
C7—C6—H6	118.5	C29—C30—C31	119.54 (18)
C8—C7—C6	119.25 (18)	C29—C30—H30	120.2
C8—C7—H7	120.4	C31—C30—H30	120.2
C6—C7—H7	120.4	N8—C31—C30	122.98 (18)
C7—C8—C9	119.05 (18)	N8—C31—H31	118.5
C7—C8—H8	120.5	C30—C31—H31	118.5
C9—C8—H8	120.5	N8—C32—C28	122.98 (16)
C19—C9—C8	118.06 (17)	N8—C32—C33	116.77 (15)
C19—C9—C10	118.78 (16)	C28—C32—C33	120.22 (16)
C8—C9—C10	123.16 (17)	N7—C33—C23	122.72 (16)
N5—C10—C13	121.65 (16)	N7—C33—C32	116.64 (15)
N5—C10—C9	117.83 (16)	C23—C33—C32	120.63 (16)
C13—C10—C9	120.52 (16)
N3—Co1—O1—C1	99.21 (14)	C13—N6—C12—C11	−0.4 (3)
N7—Co1—O1—C1	−88.09 (14)	N5—C11—C12—N6	1.1 (3)
N1—Co1—O1—C1	0.51 (13)	C12—N6—C13—C10	−0.6 (2)
N4—Co1—O1—C1	175.42 (14)	C12—N6—C13—C14	178.44 (16)
N8—Co1—O1—C1	−133.4 (3)	N5—C10—C13—N6	1.0 (3)
O1—Co1—N1—C5	−174.59 (16)	C9—C10—C13—N6	−178.97 (15)
N3—Co1—N1—C5	91.09 (15)	N5—C10—C13—C14	−178.01 (16)
N7—Co1—N1—C5	−78.04 (15)	C9—C10—C13—C14	2.0 (2)
N4—Co1—N1—C5	171.59 (15)	N6—C13—C14—C15	−0.7 (3)
N8—Co1—N1—C5	−2.37 (16)	C10—C13—C14—C15	178.29 (16)
O1—Co1—N1—C2	−2.29 (11)	N6—C13—C14—C18	−179.48 (15)
N3—Co1—N1—C2	−96.62 (12)	C10—C13—C14—C18	−0.4 (2)
N7—Co1—N1—C2	94.25 (12)	C18—C14—C15—C16	1.6 (3)
N4—Co1—N1—C2	−16.1 (2)	C13—C14—C15—C16	−177.18 (17)
N8—Co1—N1—C2	169.93 (11)	C14—C15—C16—C17	0.3 (3)
O1—Co1—N3—C6	−108.60 (15)	C18—N4—C17—C16	0.7 (3)
N7—Co1—N3—C6	101.6 (2)	Co1—N4—C17—C16	−165.11 (14)
N1—Co1—N3—C6	−29.67 (15)	C15—C16—C17—N4	−1.5 (3)
N4—Co1—N3—C6	172.09 (15)	C17—N4—C18—C14	1.4 (2)
N8—Co1—N3—C6	79.53 (15)	Co1—N4—C18—C14	169.10 (12)
O1—Co1—N3—C19	72.07 (12)	C17—N4—C18—C19	−178.96 (14)
N7—Co1—N3—C19	−77.7 (3)	Co1—N4—C18—C19	−11.25 (18)
N1—Co1—N3—C19	150.99 (11)	C15—C14—C18—N4	−2.5 (2)
N4—Co1—N3—C19	−7.25 (11)	C13—C14—C18—N4	176.31 (15)
N8—Co1—N3—C19	−99.80 (12)	C15—C14—C18—C19	177.85 (15)
O1—Co1—N4—C17	77.88 (15)	C13—C14—C18—C19	−3.3 (2)
N3—Co1—N4—C17	176.33 (15)	C6—N3—C19—C9	3.5 (2)
N7—Co1—N4—C17	−17.47 (15)	Co1—N3—C19—C9	−177.07 (12)
N1—Co1—N4—C17	91.6 (2)	C6—N3—C19—C18	−175.63 (15)
N8—Co1—N4—C17	−94.15 (15)	Co1—N3—C19—C18	3.77 (18)
O1—Co1—N4—C18	−88.50 (12)	C8—C9—C19—N3	−3.3 (2)
N3—Co1—N4—C18	9.96 (11)	C10—C9—C19—N3	176.82 (15)
N7—Co1—N4—C18	176.16 (11)	C8—C9—C19—C18	175.84 (15)
N1—Co1—N4—C18	−74.8 (2)	C10—C9—C19—C18	−4.1 (2)
N8—Co1—N4—C18	99.47 (12)	N4—C18—C19—N3	5.2 (2)
O1—Co1—N7—C20	7.01 (17)	C14—C18—C19—N3	−175.14 (14)
N3—Co1—N7—C20	156.8 (2)	N4—C18—C19—C9	−173.98 (15)
N1—Co1—N7—C20	−71.00 (16)	C14—C18—C19—C9	5.7 (2)
N4—Co1—N7—C20	88.70 (16)	C33—N7—C20—C21	−1.2 (3)
N8—Co1—N7—C20	179.53 (17)	Co1—N7—C20—C21	173.85 (15)
O1—Co1—N7—C33	−177.80 (12)	N7—C20—C21—C22	0.6 (3)
N3—Co1—N7—C33	−28.0 (3)	C20—C21—C22—C23	0.5 (3)
N1—Co1—N7—C33	104.20 (12)	C21—C22—C23—C33	−0.9 (3)
N4—Co1—N7—C33	−96.10 (12)	C21—C22—C23—C24	176.28 (19)
N8—Co1—N7—C33	−5.28 (12)	C25—N9—C24—C27	−1.2 (3)
O1—Co1—N8—C31	−127.7 (3)	C25—N9—C24—C23	−178.90 (18)
N3—Co1—N8—C31	0.04 (17)	C33—C23—C24—N9	178.66 (17)
N7—Co1—N8—C31	−174.40 (18)	C22—C23—C24—N9	1.5 (3)
N1—Co1—N8—C31	100.38 (17)	C33—C23—C24—C27	1.0 (3)
N4—Co1—N8—C31	−77.41 (17)	C22—C23—C24—C27	−176.18 (18)
O1—Co1—N8—C32	50.1 (3)	C24—N9—C25—C26	0.6 (3)
N3—Co1—N8—C32	177.92 (12)	C27—N10—C26—C25	−1.2 (3)
N7—Co1—N8—C32	3.48 (12)	N9—C25—C26—N10	0.7 (4)
N1—Co1—N8—C32	−81.74 (13)	C26—N10—C27—C24	0.5 (3)
N4—Co1—N8—C32	100.47 (12)	C26—N10—C27—C28	−179.22 (18)
Co1—O1—C1—O2	−179.64 (16)	N9—C24—C27—N10	0.7 (3)
Co1—O1—C1—C2	1.2 (2)	C23—C24—C27—N10	178.37 (17)
C5—N1—C2—C3	−1.7 (3)	N9—C24—C27—C28	−179.52 (17)
Co1—N1—C2—C3	−174.80 (15)	C23—C24—C27—C28	−1.9 (3)
C5—N1—C2—C1	176.70 (15)	N10—C27—C28—C32	179.74 (16)
Co1—N1—C2—C1	3.55 (18)	C24—C27—C28—C32	0.0 (3)
O2—C1—C2—C3	−4.0 (3)	N10—C27—C28—C29	−1.1 (3)
O1—C1—C2—C3	175.16 (17)	C24—C27—C28—C29	179.19 (18)
O2—C1—C2—N1	177.54 (17)	C32—C28—C29—C30	−0.4 (3)
O1—C1—C2—N1	−3.3 (2)	C27—C28—C29—C30	−179.66 (18)
N1—C2—C3—C4	−0.3 (3)	C28—C29—C30—C31	−1.0 (3)
C1—C2—C3—C4	−178.53 (17)	C32—N8—C31—C30	0.0 (3)
C5—N2—C4—O3	179.30 (19)	Co1—N8—C31—C30	177.86 (15)
C5—N2—C4—C3	−0.5 (3)	C29—C30—C31—N8	1.3 (3)
C2—C3—C4—O3	−178.5 (2)	C31—N8—C32—C28	−1.6 (3)
C2—C3—C4—N2	1.3 (3)	Co1—N8—C32—C28	−179.74 (13)
C2—N1—C5—O4	−177.54 (17)	C31—N8—C32—C33	176.74 (16)
Co1—N1—C5—O4	−5.6 (3)	Co1—N8—C32—C33	−1.39 (19)
C2—N1—C5—N2	2.3 (2)	C29—C28—C32—N8	1.8 (3)
Co1—N1—C5—N2	174.28 (12)	C27—C28—C32—N8	−178.94 (16)
C4—N2—C5—O4	178.55 (18)	C29—C28—C32—C33	−176.47 (16)
C4—N2—C5—N1	−1.3 (3)	C27—C28—C32—C33	2.8 (2)
C19—N3—C6—C7	−0.6 (3)	C20—N7—C33—C23	0.8 (3)
Co1—N3—C6—C7	−179.95 (14)	Co1—N7—C33—C23	−174.80 (13)
N3—C6—C7—C8	−2.4 (3)	C20—N7—C33—C32	−178.09 (16)
C6—C7—C8—C9	2.5 (3)	Co1—N7—C33—C32	6.33 (19)
C7—C8—C9—C19	0.1 (2)	C22—C23—C33—N7	0.3 (3)
C7—C8—C9—C10	−179.97 (16)	C24—C23—C33—N7	−177.03 (16)
C11—N5—C10—C13	−0.3 (3)	C22—C23—C33—C32	179.12 (16)
C11—N5—C10—C9	179.64 (16)	C24—C23—C33—C32	1.8 (3)
C19—C9—C10—N5	−179.72 (15)	N8—C32—C33—N7	−3.2 (2)
C8—C9—C10—N5	0.4 (2)	C28—C32—C33—N7	175.18 (15)
C19—C9—C10—C13	0.3 (2)	N8—C32—C33—C23	177.88 (15)
C8—C9—C10—C13	−179.64 (16)	C28—C32—C33—C23	−3.7 (2)
C10—N5—C11—C12	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H33···O4i	0.85	2.22	3.007 (3)	155
O5—H34···O6ii	0.85	2.16	2.903 (3)	146
O6—H35···O4iii	0.85	2.02	2.822 (2)	156
O6—H36···O3i	0.85	2.16	2.990 (2)	166
N2—H2···O3iv	0.83	2.03	2.850 (2)	169

Co1—O1	2.0622 (13)
Co1—N3	2.1223 (15)
Co1—N7	2.1280 (15)
Co1—N1	2.1299 (14)
Co1—N4	2.1542 (15)
Co1—N8	2.1827 (15)

O1—Co1—N3	96.18 (5)
O1—Co1—N7	96.39 (5)
N3—Co1—N7	165.47 (5)
O1—Co1—N1	78.09 (5)
N3—Co1—N1	99.75 (5)
N7—Co1—N1	89.95 (6)
O1—Co1—N4	80.99 (5)
N3—Co1—N4	77.45 (5)
N7—Co1—N4	97.38 (6)
N1—Co1—N4	158.47 (5)
O1—Co1—N8	169.75 (6)
N3—Co1—N8	90.07 (5)
N7—Co1—N8	76.48 (5)
N1—Co1—N8	108.90 (6)
N4—Co1—N8	92.51 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H33⋯O4i	0.85	2.22	3.007 (3)	155
O5—H34⋯O6ii	0.85	2.16	2.903 (3)	146
O6—H35⋯O4iii	0.85	2.02	2.822 (2)	156
O6—H36⋯O3i	0.85	2.16	2.990 (2)	166
N2—H2⋯O3iv	0.83	2.03	2.850 (2)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .