A comparative study of the interactions of cobalt(III) with naphtholate and phenolate moieties

The structural motif of piperidinium bis­[N-(2-hy­droxy­naphthalen-1-yl)­sarcosinato]­cobaltate(III), (C₅H₁₀NH₂)[Co(C₁₄H₁₃NO₃)₂], (I), displays a chain of two alternating discrete mononuclear Co^III complex anions with intervening piperidinium counter-ions. The piperidinium cations and complex anions interact via N—H...O hydrogen bonding. Each of the tridentate ligands coordinates to the Co atom in a facial mode, giving a pseudo-octahedral geometry consistent with the mixed donor-atom environment, and each complex anion exhibits C_i symmetry about the metal centre. The average Co^III—O_naphtholate distance in (I) lies within the observed range of normal values for Co^III—O_phenolate distances in related compounds, indicative of similarity of coordination behaviour between the naphtholate and phenolate moieties.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.102
• Data-to-parameter ratio = 18.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

(C5H12N)[Co(C14H13NO3)2]	Z = 2
Mr = 631.59	F(000) = 664
Triclinic, P1	Dx = 1.388 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.130 (2) Å	Cell parameters from 965 reflections
b = 11.778 (2) Å	θ = 2.5–25.8°
c = 13.065 (3) Å	µ = 0.62 mm^−1
α = 99.608 (4)°	T = 293 K
β = 90.336 (5)°	Plate, dark red
γ = 100.351 (4)°	0.18 × 0.18 × 0.02 mm
V = 1510.8 (5) Å^3

Data collection

Bruker SMART 1K CCD diffractometer	7345 independent reflections
Radiation source: fine-focus sealed tube	4286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
Tmin = 0.866, Tmax = 0.988	k = −15→15
10784 measured reflections	l = −13→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0433P)^2] where P = (Fo^2 + 2Fc^2)/3
7345 reflections	(Δ/σ)max < 0.001
392 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.35 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. The crystal structure was solved by direct methods. Non-hydrogen atoms were first refined isotropically followed by anisotropic refinement by full matrix least-squares calculation based on F². Hydrogen atoms were positioned geometrically and allowed to ride on their respective parent atoms.

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
Co1	0.5000	0.5000	0.0000	0.03210 (13)
Co2	1.0000	0.0000	0.0000	0.03259 (13)
N1	0.52068 (19)	0.67069 (15)	0.05492 (15)	0.0333 (5)
N3	−0.0514 (2)	0.43878 (17)	0.14092 (16)	0.0442 (5)
H3A	−0.0716	0.3930	0.0785	0.053*
H3B	−0.0798	0.5066	0.1391	0.053*
N1'	1.0848 (2)	0.00669 (16)	0.13937 (14)	0.0344 (5)
O1	0.41735 (17)	0.45598 (13)	0.12239 (13)	0.0404 (4)
O2	0.67372 (16)	0.50953 (13)	0.06079 (12)	0.0375 (4)
O3	0.84844 (18)	0.63830 (15)	0.13790 (16)	0.0541 (5)
O1'	0.82220 (16)	−0.03795 (13)	0.04718 (12)	0.0376 (4)
O2'	1.01584 (17)	−0.16147 (13)	−0.01968 (12)	0.0371 (4)
O3'	1.13613 (19)	−0.28116 (15)	0.03653 (14)	0.0491 (5)
C1	0.4992 (3)	0.6328 (2)	0.23650 (19)	0.0394 (6)
C2	0.4744 (3)	0.5118 (2)	0.2130 (2)	0.0401 (6)
C3	0.5113 (3)	0.4465 (3)	0.2878 (2)	0.0541 (8)
H3	0.4921	0.3650	0.2741	0.065*
C4	0.5745 (3)	0.5028 (3)	0.3792 (2)	0.0616 (9)
H4	0.5976	0.4588	0.4270	0.074*
C5	0.6060 (3)	0.6263 (3)	0.4036 (2)	0.0540 (8)
C6	0.6755 (3)	0.6850 (4)	0.4977 (2)	0.0776 (11)
H6	0.7024	0.6417	0.5447	0.093*
C7	0.7029 (4)	0.8032 (4)	0.5193 (3)	0.0910 (13)
H7	0.7492	0.8406	0.5809	0.109*
C8	0.6624 (4)	0.8697 (3)	0.4503 (3)	0.0876 (13)
H8	0.6804	0.9510	0.4668	0.105*
C9	0.5971 (3)	0.8167 (3)	0.3592 (2)	0.0654 (9)
H9	0.5716	0.8627	0.3140	0.079*
C10	0.5665 (3)	0.6931 (2)	0.3311 (2)	0.0464 (7)
C11	0.4503 (3)	0.6919 (2)	0.15499 (19)	0.0383 (6)
H11A	0.4638	0.7755	0.1804	0.046*
H11B	0.3547	0.6637	0.1421	0.046*
C12	0.7360 (3)	0.6146 (2)	0.0945 (2)	0.0380 (6)
C13	0.6678 (2)	0.7120 (2)	0.0730 (2)	0.0405 (6)
H13A	0.6842	0.7759	0.1315	0.049*
H13B	0.7054	0.7412	0.0122	0.049*
C14	0.4689 (3)	0.7390 (2)	−0.0176 (2)	0.0420 (6)
H14A	0.3740	0.7122	−0.0298	0.063*
H14B	0.5134	0.7282	−0.0822	0.063*
H14C	0.4859	0.8206	0.0125	0.063*
C100	−0.1248 (3)	0.3802 (2)	0.2213 (2)	0.0558 (8)
H10B	−0.1026	0.3031	0.2184	0.067*
H10A	−0.2207	0.3706	0.2074	0.067*
C101	−0.0893 (3)	0.4505 (3)	0.3278 (2)	0.0648 (9)
H10D	−0.1331	0.4077	0.3793	0.078*
H10C	−0.1217	0.5239	0.3334	0.078*
C102	0.0611 (3)	0.4755 (3)	0.3493 (2)	0.0722 (10)
H10E	0.0821	0.5252	0.4165	0.087*
H10F	0.0924	0.4027	0.3511	0.087*
C103	0.1321 (3)	0.5356 (3)	0.2659 (2)	0.0619 (8)
H10G	0.1069	0.6117	0.2686	0.074*
H10H	0.2284	0.5478	0.2788	0.074*
C104	0.0963 (3)	0.4635 (2)	0.1591 (2)	0.0504 (7)
H10I	0.1385	0.5060	0.1067	0.061*
H10J	0.1294	0.3905	0.1537	0.061*
C1'	0.8691 (3)	0.0334 (2)	0.22648 (19)	0.0382 (6)
C2'	0.7879 (3)	0.0182 (2)	0.13762 (19)	0.0367 (6)
C3'	0.6642 (3)	0.0579 (2)	0.1440 (2)	0.0463 (7)
H3'	0.6086	0.0463	0.0849	0.056*
C4'	0.6252 (3)	0.1133 (2)	0.2364 (2)	0.0527 (7)
H4'	0.5424	0.1371	0.2392	0.063*
C5'	0.7076 (3)	0.1351 (2)	0.3274 (2)	0.0491 (7)
C6'	0.6693 (4)	0.1942 (3)	0.4230 (3)	0.0645 (9)
H6'	0.5869	0.2186	0.4265	0.077*
C7'	0.7509 (4)	0.2157 (3)	0.5096 (3)	0.0740 (10)
H7'	0.7238	0.2543	0.5717	0.089*
C8'	0.8752 (4)	0.1802 (3)	0.5054 (2)	0.0724 (10)
H8'	0.9317	0.1973	0.5645	0.087*
C9'	0.9148 (3)	0.1202 (2)	0.4151 (2)	0.0568 (8)
H9'	0.9967	0.0949	0.4144	0.068*
C10'	0.8327 (3)	0.0959 (2)	0.3227 (2)	0.0445 (7)
C11'	0.9832 (3)	−0.0320 (2)	0.21562 (19)	0.0418 (6)
H11C	0.9474	−0.1147	0.1940	0.050*
H11D	1.0282	−0.0225	0.2831	0.050*
C12'	1.1038 (3)	−0.1847 (2)	0.04149 (19)	0.0374 (6)
C13'	1.1721 (3)	−0.0823 (2)	0.12118 (18)	0.0400 (6)
H13C	1.1885	−0.1089	0.1857	0.048*
H13D	1.2578	−0.0484	0.0963	0.048*
C14'	1.1652 (3)	0.1232 (2)	0.18172 (19)	0.0459 (7)
H14F	1.2190	0.1172	0.2407	0.069*
H14D	1.1062	0.1774	0.2026	0.069*
H14E	1.2227	0.1504	0.1293	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0266 (3)	0.0298 (2)	0.0411 (3)	0.0041 (2)	0.0018 (2)	0.0104 (2)
Co2	0.0352 (3)	0.0300 (2)	0.0315 (3)	0.0033 (2)	−0.0018 (2)	0.0053 (2)
N1	0.0285 (12)	0.0309 (10)	0.0428 (12)	0.0068 (9)	0.0012 (9)	0.0109 (9)
N3	0.0471 (15)	0.0379 (12)	0.0479 (14)	0.0102 (10)	−0.0017 (11)	0.0058 (10)
N1'	0.0344 (12)	0.0362 (11)	0.0313 (11)	0.0049 (9)	0.0010 (9)	0.0038 (9)
O1	0.0396 (11)	0.0353 (9)	0.0457 (11)	0.0012 (8)	0.0060 (8)	0.0112 (8)
O2	0.0312 (10)	0.0346 (9)	0.0486 (11)	0.0069 (8)	0.0016 (8)	0.0119 (8)
O3	0.0308 (11)	0.0448 (11)	0.0861 (15)	0.0032 (8)	−0.0125 (10)	0.0137 (10)
O1'	0.0357 (10)	0.0379 (9)	0.0356 (10)	0.0000 (8)	0.0001 (7)	0.0035 (8)
O2'	0.0415 (11)	0.0331 (9)	0.0362 (10)	0.0071 (8)	−0.0031 (8)	0.0044 (7)
O3'	0.0515 (13)	0.0433 (10)	0.0561 (12)	0.0198 (9)	0.0016 (9)	0.0070 (9)
C1	0.0336 (15)	0.0437 (15)	0.0408 (15)	0.0035 (12)	0.0030 (11)	0.0108 (12)
C2	0.0303 (15)	0.0478 (15)	0.0445 (16)	0.0060 (12)	0.0106 (12)	0.0155 (13)
C3	0.063 (2)	0.0557 (17)	0.0544 (19)	0.0219 (15)	0.0152 (15)	0.0273 (15)
C4	0.065 (2)	0.088 (2)	0.0464 (19)	0.0326 (19)	0.0091 (15)	0.0327 (17)
C5	0.0418 (18)	0.079 (2)	0.0443 (17)	0.0115 (16)	0.0055 (13)	0.0199 (15)
C6	0.055 (2)	0.130 (3)	0.048 (2)	0.000 (2)	−0.0022 (16)	0.031 (2)
C7	0.070 (3)	0.132 (4)	0.050 (2)	−0.031 (3)	−0.0085 (18)	0.009 (2)
C8	0.100 (3)	0.091 (3)	0.049 (2)	−0.038 (2)	0.0002 (19)	0.0053 (19)
C9	0.074 (2)	0.065 (2)	0.0461 (18)	−0.0141 (17)	−0.0006 (16)	0.0066 (15)
C10	0.0372 (16)	0.0592 (17)	0.0403 (16)	−0.0014 (13)	0.0060 (12)	0.0118 (13)
C11	0.0340 (15)	0.0373 (13)	0.0450 (16)	0.0121 (11)	0.0040 (11)	0.0050 (12)
C12	0.0304 (15)	0.0385 (14)	0.0469 (16)	0.0059 (12)	0.0064 (12)	0.0128 (12)
C13	0.0305 (15)	0.0327 (13)	0.0584 (17)	0.0010 (11)	0.0009 (12)	0.0132 (12)
C14	0.0463 (17)	0.0322 (13)	0.0514 (17)	0.0102 (12)	−0.0022 (13)	0.0156 (12)
C100	0.0408 (18)	0.0582 (18)	0.068 (2)	0.0001 (14)	0.0066 (14)	0.0179 (16)
C101	0.056 (2)	0.081 (2)	0.055 (2)	0.0011 (17)	0.0165 (15)	0.0136 (17)
C102	0.065 (2)	0.100 (3)	0.050 (2)	0.013 (2)	−0.0070 (16)	0.0109 (18)
C103	0.0382 (18)	0.082 (2)	0.058 (2)	0.0010 (16)	0.0028 (14)	0.0013 (17)
C104	0.0391 (17)	0.0549 (17)	0.0579 (19)	0.0097 (14)	0.0077 (13)	0.0102 (14)
C1'	0.0387 (16)	0.0374 (13)	0.0392 (15)	0.0048 (12)	0.0065 (12)	0.0103 (11)
C2'	0.0380 (16)	0.0310 (13)	0.0410 (15)	0.0015 (11)	0.0039 (11)	0.0114 (11)
C3'	0.0404 (17)	0.0442 (15)	0.0566 (18)	0.0076 (13)	0.0015 (13)	0.0156 (14)
C4'	0.0461 (19)	0.0457 (16)	0.071 (2)	0.0163 (14)	0.0133 (15)	0.0153 (15)
C5'	0.054 (2)	0.0403 (15)	0.0527 (18)	0.0079 (14)	0.0159 (14)	0.0071 (13)
C6'	0.069 (2)	0.0537 (19)	0.070 (2)	0.0138 (17)	0.0298 (18)	0.0057 (17)
C7'	0.086 (3)	0.067 (2)	0.058 (2)	0.003 (2)	0.0265 (19)	−0.0087 (17)
C8'	0.075 (3)	0.083 (2)	0.045 (2)	−0.004 (2)	0.0095 (17)	−0.0076 (17)
C9'	0.054 (2)	0.0669 (19)	0.0427 (17)	0.0004 (15)	0.0062 (14)	0.0022 (15)
C10'	0.0498 (18)	0.0398 (14)	0.0417 (16)	0.0019 (13)	0.0109 (13)	0.0074 (12)
C11'	0.0467 (17)	0.0476 (15)	0.0306 (14)	0.0051 (13)	−0.0005 (12)	0.0096 (12)
C12'	0.0347 (15)	0.0408 (14)	0.0386 (15)	0.0092 (12)	0.0068 (11)	0.0094 (12)
C13'	0.0390 (16)	0.0457 (15)	0.0370 (15)	0.0103 (12)	−0.0038 (11)	0.0090 (12)
C14'	0.0499 (18)	0.0426 (15)	0.0389 (15)	−0.0004 (13)	−0.0065 (13)	−0.0014 (12)

Geometric parameters (Å, º)

Co1—O2^i	1.9033 (16)	C11—H11B	0.9700
Co1—O2	1.9033 (16)	C12—C13	1.503 (3)
Co1—O1^i	1.9139 (17)	C13—H13A	0.9700
Co1—O1	1.9139 (17)	C13—H13B	0.9700
Co1—N1	1.9915 (18)	C14—H14A	0.9600
Co1—N1^i	1.9915 (18)	C14—H14B	0.9600
Co2—O1'^ii	1.9076 (17)	C14—H14C	0.9600
Co2—O1'	1.9076 (17)	C100—C101	1.501 (4)
Co2—O2'^ii	1.9120 (15)	C100—H10B	0.9700
Co2—O2'	1.9120 (15)	C100—H10A	0.9700
Co2—N1'^ii	1.9922 (18)	C101—C102	1.514 (4)
Co2—N1'	1.9922 (18)	C101—H10D	0.9700
N1—C13	1.486 (3)	C101—H10C	0.9700
N1—C14	1.490 (3)	C102—C103	1.513 (4)
N1—C11	1.499 (3)	C102—H10E	0.9700
N3—C104	1.482 (3)	C102—H10F	0.9700
N3—C100	1.483 (3)	C103—C104	1.513 (4)
N3—H3A	0.9000	C103—H10G	0.9700
N3—H3B	0.9000	C103—H10H	0.9700
N1'—C13'	1.480 (3)	C104—H10I	0.9700
N1'—C14'	1.481 (3)	C104—H10J	0.9700
N1'—C11'	1.501 (3)	C1'—C2'	1.387 (3)
O1—C2	1.328 (3)	C1'—C10'	1.433 (3)
O2—C12	1.288 (3)	C1'—C11'	1.496 (3)
O3—C12	1.234 (3)	C2'—C3'	1.412 (3)
O1'—C2'	1.335 (3)	C3'—C4'	1.369 (4)
O2'—C12'	1.288 (3)	C3'—H3'	0.9300
O3'—C12'	1.230 (3)	C4'—C5'	1.410 (4)
C1—C2	1.384 (3)	C4'—H4'	0.9300
C1—C10	1.421 (3)	C5'—C6'	1.416 (4)
C1—C11	1.493 (3)	C5'—C10'	1.422 (4)
C2—C3	1.427 (3)	C6'—C7'	1.358 (4)
C3—C4	1.359 (4)	C6'—H6'	0.9300
C3—H3	0.9300	C7'—C8'	1.395 (5)
C4—C5	1.412 (4)	C7'—H7'	0.9300
C4—H4	0.9300	C8'—C9'	1.372 (4)
C5—C6	1.420 (4)	C8'—H8'	0.9300
C5—C10	1.426 (4)	C9'—C10'	1.421 (4)
C6—C7	1.350 (5)	C9'—H9'	0.9300
C6—H6	0.9300	C11'—H11C	0.9700
C7—C8	1.394 (5)	C11'—H11D	0.9700
C7—H7	0.9300	C12'—C13'	1.513 (3)
C8—C9	1.356 (4)	C13'—H13C	0.9700
C8—H8	0.9300	C13'—H13D	0.9700
C9—C10	1.417 (4)	C14'—H14F	0.9600
C9—H9	0.9300	C14'—H14D	0.9600
C11—H11A	0.9700	C14'—H14E	0.9600
O2^i—Co1—O2	180.00 (11)	N1—C13—H13A	109.4
O2^i—Co1—O1^i	90.86 (7)	C12—C13—H13A	109.4
O2—Co1—O1^i	89.14 (7)	N1—C13—H13B	109.4
O2^i—Co1—O1	89.14 (7)	C12—C13—H13B	109.4
O2—Co1—O1	90.86 (7)	H13A—C13—H13B	108.0
O1^i—Co1—O1	180.0	N1—C14—H14A	109.5
O2^i—Co1—N1	93.57 (7)	N1—C14—H14B	109.5
O2—Co1—N1	86.43 (7)	H14A—C14—H14B	109.5
O1^i—Co1—N1	86.67 (7)	N1—C14—H14C	109.5
O1—Co1—N1	93.33 (7)	H14A—C14—H14C	109.5
O2^i—Co1—N1^i	86.43 (7)	H14B—C14—H14C	109.5
O2—Co1—N1^i	93.57 (7)	N3—C100—C101	111.0 (2)
O1^i—Co1—N1^i	93.33 (7)	N3—C100—H10B	109.4
O1—Co1—N1^i	86.67 (7)	C101—C100—H10B	109.4
N1—Co1—N1^i	180.0	N3—C100—H10A	109.4
O1'^ii—Co2—O1'	180.00 (9)	C101—C100—H10A	109.4
O1'^ii—Co2—O2'^ii	90.42 (7)	H10B—C100—H10A	108.0
O1'—Co2—O2'^ii	89.58 (7)	C100—C101—C102	111.1 (3)
O1'^ii—Co2—O2'	89.58 (7)	C100—C101—H10D	109.4
O1'—Co2—O2'	90.42 (7)	C102—C101—H10D	109.4
O2'^ii—Co2—O2'	180.00 (10)	C100—C101—H10C	109.4
O1'^ii—Co2—N1'^ii	93.34 (8)	C102—C101—H10C	109.4
O1'—Co2—N1'^ii	86.66 (8)	H10D—C101—H10C	108.0
O2'^ii—Co2—N1'^ii	84.10 (7)	C103—C102—C101	110.3 (2)
O2'—Co2—N1'^ii	95.90 (7)	C103—C102—H10E	109.6
O1'^ii—Co2—N1'	86.66 (8)	C101—C102—H10E	109.6
O1'—Co2—N1'	93.34 (8)	C103—C102—H10F	109.6
O2'^ii—Co2—N1'	95.90 (7)	C101—C102—H10F	109.6
O2'—Co2—N1'	84.10 (7)	H10E—C102—H10F	108.1
N1'^ii—Co2—N1'	180.00 (5)	C104—C103—C102	111.2 (3)
C13—N1—C14	109.24 (18)	C104—C103—H10G	109.4
C13—N1—C11	110.05 (19)	C102—C103—H10G	109.4
C14—N1—C11	107.54 (19)	C104—C103—H10H	109.4
C13—N1—Co1	104.84 (14)	C102—C103—H10H	109.4
C14—N1—Co1	114.10 (15)	H10G—C103—H10H	108.0
C11—N1—Co1	111.05 (14)	N3—C104—C103	109.8 (2)
C104—N3—C100	113.4 (2)	N3—C104—H10I	109.7
C104—N3—H3A	108.9	C103—C104—H10I	109.7
C100—N3—H3A	108.9	N3—C104—H10J	109.7
C104—N3—H3B	108.9	C103—C104—H10J	109.7
C100—N3—H3B	108.9	H10I—C104—H10J	108.2
H3A—N3—H3B	107.7	C2'—C1'—C10'	120.5 (3)
C13'—N1'—C14'	110.41 (19)	C2'—C1'—C11'	114.8 (2)
C13'—N1'—C11'	106.75 (18)	C10'—C1'—C11'	124.2 (2)
C14'—N1'—C11'	110.54 (19)	O1'—C2'—C1'	120.9 (2)
C13'—N1'—Co2	103.87 (13)	O1'—C2'—C3'	119.6 (2)
C14'—N1'—Co2	113.08 (14)	C1'—C2'—C3'	119.5 (2)
C11'—N1'—Co2	111.81 (15)	C4'—C3'—C2'	120.7 (3)
C2—O1—Co1	116.88 (15)	C4'—C3'—H3'	119.6
C12—O2—Co1	114.45 (15)	C2'—C3'—H3'	119.6
C2'—O1'—Co2	120.15 (14)	C3'—C4'—C5'	121.5 (3)
C12'—O2'—Co2	114.27 (15)	C3'—C4'—H4'	119.2
C2—C1—C10	121.3 (2)	C5'—C4'—H4'	119.2
C2—C1—C11	114.5 (2)	C4'—C5'—C6'	122.0 (3)
C10—C1—C11	124.2 (2)	C4'—C5'—C10'	118.7 (3)
O1—C2—C1	121.1 (2)	C6'—C5'—C10'	119.3 (3)
O1—C2—C3	119.8 (2)	C7'—C6'—C5'	121.2 (3)
C1—C2—C3	119.1 (2)	C7'—C6'—H6'	119.4
C4—C3—C2	120.2 (3)	C5'—C6'—H6'	119.4
C4—C3—H3	119.9	C6'—C7'—C8'	120.1 (3)
C2—C3—H3	119.9	C6'—C7'—H7'	119.9
C3—C4—C5	122.0 (3)	C8'—C7'—H7'	119.9
C3—C4—H4	119.0	C9'—C8'—C7'	120.6 (3)
C5—C4—H4	119.0	C9'—C8'—H8'	119.7
C4—C5—C6	121.9 (3)	C7'—C8'—H8'	119.7
C4—C5—C10	118.6 (3)	C8'—C9'—C10'	121.1 (3)
C6—C5—C10	119.5 (3)	C8'—C9'—H9'	119.5
C7—C6—C5	120.5 (3)	C10'—C9'—H9'	119.5
C7—C6—H6	119.8	C9'—C10'—C5'	117.7 (3)
C5—C6—H6	119.8	C9'—C10'—C1'	123.3 (3)
C6—C7—C8	120.7 (3)	C5'—C10'—C1'	119.0 (2)
C6—C7—H7	119.6	C1'—C11'—N1'	114.11 (19)
C8—C7—H7	119.6	C1'—C11'—H11C	108.7
C9—C8—C7	120.4 (3)	N1'—C11'—H11C	108.7
C9—C8—H8	119.8	C1'—C11'—H11D	108.7
C7—C8—H8	119.8	N1'—C11'—H11D	108.7
C8—C9—C10	121.8 (3)	H11C—C11'—H11D	107.6
C8—C9—H9	119.1	O3'—C12'—O2'	124.5 (2)
C10—C9—H9	119.1	O3'—C12'—C13'	120.0 (2)
C9—C10—C1	124.2 (2)	O2'—C12'—C13'	115.5 (2)
C9—C10—C5	117.1 (3)	N1'—C13'—C12'	109.16 (19)
C1—C10—C5	118.7 (3)	N1'—C13'—H13C	109.8
C1—C11—N1	112.7 (2)	C12'—C13'—H13C	109.8
C1—C11—H11A	109.1	N1'—C13'—H13D	109.8
N1—C11—H11A	109.1	C12'—C13'—H13D	109.8
C1—C11—H11B	109.1	H13C—C13'—H13D	108.3
N1—C11—H11B	109.1	N1'—C14'—H14F	109.5
H11A—C11—H11B	107.8	N1'—C14'—H14D	109.5
O3—C12—O2	123.9 (2)	H14F—C14'—H14D	109.5
O3—C12—C13	119.7 (2)	N1'—C14'—H14E	109.5
O2—C12—C13	116.4 (2)	H14F—C14'—H14E	109.5
N1—C13—C12	111.08 (18)	H14D—C14'—H14E	109.5
O2^i—Co1—N1—C13	−159.50 (14)	C11—C1—C10—C5	178.9 (3)
O2—Co1—N1—C13	20.50 (14)	C4—C5—C10—C9	178.6 (3)
O1^i—Co1—N1—C13	−68.85 (15)	C6—C5—C10—C9	−1.5 (4)
O1—Co1—N1—C13	111.15 (15)	C4—C5—C10—C1	−1.1 (4)
O2^i—Co1—N1—C14	−40.03 (17)	C6—C5—C10—C1	178.9 (3)
O2—Co1—N1—C14	139.97 (17)	C2—C1—C11—N1	−64.2 (3)
O1^i—Co1—N1—C14	50.62 (17)	C10—C1—C11—N1	115.5 (3)
O1—Co1—N1—C14	−129.38 (17)	C13—N1—C11—C1	−58.1 (2)
O2^i—Co1—N1—C11	81.69 (15)	C14—N1—C11—C1	−176.9 (2)
O2—Co1—N1—C11	−98.31 (15)	Co1—N1—C11—C1	57.6 (2)
O1^i—Co1—N1—C11	172.34 (15)	Co1—O2—C12—O3	178.6 (2)
O1—Co1—N1—C11	−7.66 (15)	Co1—O2—C12—C13	−4.8 (3)
O1'^ii—Co2—N1'—C13'	−58.85 (14)	C14—N1—C13—C12	−149.9 (2)
O1'—Co2—N1'—C13'	121.15 (14)	C11—N1—C13—C12	92.2 (2)
O2'^ii—Co2—N1'—C13'	−148.93 (14)	Co1—N1—C13—C12	−27.2 (2)
O2'—Co2—N1'—C13'	31.07 (14)	O3—C12—C13—N1	−160.6 (2)
O1'^ii—Co2—N1'—C14'	60.86 (17)	O2—C12—C13—N1	22.8 (3)
O1'—Co2—N1'—C14'	−119.14 (17)	C104—N3—C100—C101	55.8 (3)
O2'^ii—Co2—N1'—C14'	−29.22 (18)	N3—C100—C101—C102	−54.7 (3)
O2'—Co2—N1'—C14'	150.78 (18)	C100—C101—C102—C103	55.6 (4)
O1'^ii—Co2—N1'—C11'	−173.60 (16)	C101—C102—C103—C104	−56.4 (4)
O1'—Co2—N1'—C11'	6.40 (16)	C100—N3—C104—C103	−55.9 (3)
O2'^ii—Co2—N1'—C11'	96.32 (16)	C102—C103—C104—N3	55.9 (3)
O2'—Co2—N1'—C11'	−83.68 (16)	Co2—O1'—C2'—C1'	−47.4 (3)
O2^i—Co1—O1—C2	−139.14 (17)	Co2—O1'—C2'—C3'	135.55 (19)
O2—Co1—O1—C2	40.86 (17)	C10'—C1'—C2'—O1'	178.7 (2)
N1—Co1—O1—C2	−45.62 (17)	C11'—C1'—C2'—O1'	−8.6 (3)
N1^i—Co1—O1—C2	134.38 (17)	C10'—C1'—C2'—C3'	−4.3 (3)
O1^i—Co1—O2—C12	77.07 (17)	C11'—C1'—C2'—C3'	168.4 (2)
O1—Co1—O2—C12	−102.93 (17)	O1'—C2'—C3'—C4'	178.5 (2)
N1—Co1—O2—C12	−9.65 (17)	C1'—C2'—C3'—C4'	1.4 (4)
N1^i—Co1—O2—C12	170.35 (17)	C2'—C3'—C4'—C5'	1.5 (4)
O2'^ii—Co2—O1'—C2'	−52.47 (17)	C3'—C4'—C5'—C6'	178.9 (3)
O2'—Co2—O1'—C2'	127.53 (17)	C3'—C4'—C5'—C10'	−1.4 (4)
N1'^ii—Co2—O1'—C2'	−136.58 (17)	C4'—C5'—C6'—C7'	−179.1 (3)
N1'—Co2—O1'—C2'	43.42 (17)	C10'—C5'—C6'—C7'	1.1 (4)
O1'^ii—Co2—O2'—C12'	66.14 (18)	C5'—C6'—C7'—C8'	0.3 (5)
O1'—Co2—O2'—C12'	−113.86 (18)	C6'—C7'—C8'—C9'	−2.0 (5)
N1'^ii—Co2—O2'—C12'	159.45 (17)	C7'—C8'—C9'—C10'	2.1 (5)
N1'—Co2—O2'—C12'	−20.55 (17)	C8'—C9'—C10'—C5'	−0.6 (4)
Co1—O1—C2—C1	53.8 (3)	C8'—C9'—C10'—C1'	−179.9 (3)
Co1—O1—C2—C3	−126.1 (2)	C4'—C5'—C10'—C9'	179.3 (2)
C10—C1—C2—O1	−176.7 (2)	C6'—C5'—C10'—C9'	−1.0 (4)
C11—C1—C2—O1	3.0 (4)	C4'—C5'—C10'—C1'	−1.5 (4)
C10—C1—C2—C3	3.2 (4)	C6'—C5'—C10'—C1'	178.3 (2)
C11—C1—C2—C3	−177.0 (2)	C2'—C1'—C10'—C9'	−176.5 (2)
O1—C2—C3—C4	177.5 (3)	C11'—C1'—C10'—C9'	11.5 (4)
C1—C2—C3—C4	−2.5 (4)	C2'—C1'—C10'—C5'	4.3 (4)
C2—C3—C4—C5	−0.1 (5)	C11'—C1'—C10'—C5'	−167.7 (2)
C3—C4—C5—C6	−178.1 (3)	C2'—C1'—C11'—N1'	64.3 (3)
C3—C4—C5—C10	1.9 (5)	C10'—C1'—C11'—N1'	−123.3 (2)
C4—C5—C6—C7	−179.2 (3)	C13'—N1'—C11'—C1'	−167.81 (19)
C10—C5—C6—C7	0.8 (5)	C14'—N1'—C11'—C1'	72.1 (3)
C5—C6—C7—C8	0.6 (6)	Co2—N1'—C11'—C1'	−54.9 (2)
C6—C7—C8—C9	−1.3 (6)	Co2—O2'—C12'—O3'	−174.6 (2)
C7—C8—C9—C10	0.5 (6)	Co2—O2'—C12'—C13'	3.4 (3)
C8—C9—C10—C1	−179.5 (3)	C14'—N1'—C13'—C12'	−157.6 (2)
C8—C9—C10—C5	0.8 (5)	C11'—N1'—C13'—C12'	82.2 (2)
C2—C1—C10—C9	178.9 (3)	Co2—N1'—C13'—C12'	−36.1 (2)
C11—C1—C10—C9	−0.8 (4)	O3'—C12'—C13'—N1'	−158.5 (2)
C2—C1—C10—C5	−1.5 (4)	O2'—C12'—C13'—N1'	23.5 (3)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3′^iii	0.90	1.85	2.743 (3)	169
N3—H3B···O3^iv	0.90	1.83	2.728 (3)	175

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